@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/106094,
    title ="Multilabel Classification Models for the Prediction of Cross-Coupling Reaction Conditions",
    author = "Maser, Michael R. and Cui, Alexander Y.",
    journal = "Journal of Chemical Information and Modeling",
    volume = "61",
    number = "1",
    pages = "156-166",
    month = "January",
    year = "2021",
    doi = "10.1021/acs.jcim.0c01234",
    issn = "1549-9596",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20201015-152733539",
    note = "© 2021 American Chemical Society. \n\nReceived: October 23, 2020; Publication Date: January 8, 2021. \n\nWe thank Prof Pietro Perona for mentorship guidance and helpful project discussions and Chase Blagden for help in structuring the GBM experiments. Fellowship support was provided by the NSF (M.R.M., T.J.D. Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Y.Y. is supported in part by NSF 1645832 and NSF 1918839 and funding from Raytheon and Beyond Limits. S.R. is supported by grants from Disney Research and from Nissan Corporation. Financial support from Research Corporation is warmly acknowledged. \n\nAuthor Contributions: M.R.M., A.Y.C., and S.R. contributed equally to this work. \n\nThe authors declare no competing financial interest.",
    revision_no = "36",
    abstract = "Machine-learned ranking models have been developed for the prediction of substrate-specific cross-coupling reaction conditions. Data sets of published reactions were curated for Suzuki, Negishi, and C–N couplings, as well as Pauson–Khand reactions. String, descriptor, and graph encodings were tested as input representations, and models were trained to predict the set of conditions used in a reaction as a binary vector. Unique reagent dictionaries categorized by expert-crafted reaction roles were constructed for each data set, leading to context-aware predictions. We find that relational graph convolutional networks and gradient-boosting machines are very effective for this learning task, and we disclose a novel reaction-level graph attention operation in the top-performing model.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/106097,
    title ="A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core",
    author = "Cowper, Nicholas G. W. and Hesse, Matthew J.",
    journal = "Chemical Science",
    volume = "11",
    number = "43",
    pages = "11897-11901",
    month = "November",
    year = "2020",
    doi = "10.1039/d0sc04802j",
    issn = "2041-6520",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20201015-152733817",
    note = "© The Author(s) 2020. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. \n\nReceived 1st September 2020. Accepted 3rd October 2020. \nFirst published\t15 Oct 2020. \n\nAll publication charges for this article have been paid for by the Royal Society of Chemistry. \n\nWe gratefully acknowledge Dr Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, Dr David VanderVelde for assistance with NMR structure analysis, and Dr Michael K. Takase for X-ray crystallographic structure determination. We thank Materia, Inc. for donations of metathesis catalysts. S. E. R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is gratefully acknowledged. \n\nThere are no conflicts to declare.",
    revision_no = "21",
    abstract = "The bicyclic tetrahydro-1,2-oxazine subunit of gliovirin is synthesized through a diastereoselective copper-catalyzed cyclization of an N-hydroxyamino ester. Oxidative elaboration to the fully functionalized bicycle was achieved through a series of mild transformations. Central to this approach was the development of the first catalytic, enantioselective propargylation of an oxime to furnish a key N-hydroyxamino ester intermediate.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/105531,
    title ="Synthesis and Biological Evaluation of Pyrroloindolines as Positive Allosteric Modulators of the α1β2γ2 GABA_A Receptor",
    author = "Blom, Annet E. M. and Su, Justin Y.",
    journal = "ACS Medicinal Chemistry Letters",
    volume = "11",
    number = "11",
    pages = "2204-2211",
    month = "November",
    year = "2020",
    doi = "10.1021/acsmedchemlett.0c00340",
    issn = "1948-5875",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200924-152452617",
    note = "© 2020 American Chemical Society. \n\nReceived 18 June 2020. Accepted 15 September 2020. Published online 21 September 2020. \n\nWe thank Alex Maolanon and Katie Chan for early synthesis efforts, as well as Chris B. Marotta and Kristina Daeffler for performing the preliminary Cys-loop screen. We are grateful to Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and assistance with performing preparative chiral HPLC and SFC resolutions. S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (S.E.R. R35GM118191-01) is gratefully acknowledged. \n\nAuthor Contributions. All authors have given approval to the final version of the manuscript. \n\nThe authors declare no competing financial interest.",
    revision_no = "23",
    abstract = "γ-Aminobutyric acid type A (GABA_A) receptors are key mediators of central inhibitory neurotransmission and have been implicated in several disorders of the central nervous system. Some positive allosteric modulators (PAMs) of this receptor provide great therapeutic benefits to patients. However, adverse effects remain a challenge. Selective targeting of GABA_A receptors could mitigate this problem. Here, we describe the synthesis and functional evaluation of a novel series of pyrroloin-dolines that display significant modulation of the GABA_A receptor, acting as PAMs. We found that halogen incorporation at the C5 position greatly increased the PAM potency relative to the parent ligand, while substitutions at other positions generally decreased potency. Mutagenesis studies suggest that the binding site lies at the top of the transmembrane domain.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/107715,
    title ="Asymmetric Michael Addition of Dimethyl Malonate to 2 Cyclopenten-1-one Catalyzed by a Heterobimetallic Complex",
    author = "Fastuca, Nicholas J. and Wong, Alice R.",
    journal = "Organic Syntheses",
    volume = "97",
    
    pages = "327-338",
    month = "November",
    year = "2020",
    doi = "10.15227/orgsyn.097.0327",
    issn = "2333-3553",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20210125-140300975",
    note = "© 2020 Organic Syntheses, Inc. \n\nPublished on the Web 11/6/2020.\n\n",
    revision_no = "7",
    abstract = "A. Preparation of GaNa-(S)-BINOL((S)-2) Solution (0.05 M).2 A flame-dried 1L, three-necked round-bottomed flask with 24/40 joints and a 1.5\" Teflon coated egg-shaped magnetic stir bar is brought into a nitrogen filled glovebox (Note 2). The flask is charged with gallium (III) chloride (5.0 g, 28.4 mmol, 1.0 equiv) (Notes 3 and 4). The flask is sealed with three rubber septa (one of which is fitted with an internal temperature probe) brought out of the glovebox, and put under positive pressure of nitrogen via a needle attached to a nitrogen line. Another flame-dried 1L, three-necked round-bottomed flask with 24/40 joints and a 1.5\" Teflon coated egg-shaped magnetic stir bar is charged with (S)-(-)-1,1'-bi(2-naphthol) ((S)-BINOL, (S)-1) (16.26 g, 56.8 mmol, 2.0 equiv) (Note 5). The flask is sealed with three rubber septa (one of which is fitted with a thermometer) and evacuated and backfilled with nitrogen three times (5 minutes under vacuum per cycle). A flame-dried 500 mL round-bottomed flask with a 24/40 joint and a 1\" Teflon coated egg-shaped magnetic stir bar is charged with sodium tert -butoxide (10.92 g, 113.6 mmol, 4.0 equiv) (Note 6). The flask is sealed with a rubber septum and evacuated and backfilled with nitrogen three times (5 minutes under vacuum per cycle).",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/104893,
    title ="Organic Chemistry: A Call to Action for Diversity and Inclusion",
    author = "Reisman, Sarah E. and Sarpong, Richmond",
    journal = "ACS Central Science",
    volume = "6",
    number = "8",
    pages = "1241-1247",
    month = "August",
    year = "2020",
    doi = "10.1021/acscentsci.0c01027",
    issn = "2374-7943",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200810-143641171",
    note = "© 2020 American Chemical Society. ACS AuthorChoice. \n\nPublished: August 10, 2020.\n\nWe thank the students from each of our groups for their invaluable advice and feedback as we wrote this Editorial, including Hanna Clements (U of Utah), Kristen Gardner (UC Berkeley), Shane Lies (UW Madison), and Brandon Wright (UC Berkeley). In addition, we are grateful to all of the students in our groups, who have taught us so much over the years about being better mentors. We are indebted to Prof. Brian Stoltz (Caltech) and Prof. F. Dean Toste (UC Berkeley) for their important contributions in the early stages of writing this Editorial. \n\nThis Editorial came about after significant private conversations among many of us in the organic chemistry community following the publication of the Hudlicky Perspective. After these discussions about the persistent, baseless premises, we realized that it would be important for members of our field to repudiate them. Although we are all rightfully proud that the science of organic chemistry has made revolutionary advances over the last three decades, we have not yet succeeded in uprooting our field’s problematic history of unhealthy, exclusionary practices. We view this moment as an opportunity to initiate substantive change. We must act to realize a more diverse, equitable, and inclusive culture in the field of organic chemistry. \n\nViews expressed in this editorial are those of the authors and not necessarily the views of the ACS. \n\nThis Editorial is jointly published in The Journal of Organic Chemistry, Organic Letters, ACS Central Science, and Organometallics.",
    revision_no = "18",
    abstract = "By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/104891,
    title ="Organic Chemistry: A Call to Action for Diversity and Inclusion",
    author = "Reisman, Sarah E. and Sarpong, Richmond",
    journal = "Organometallics",
    volume = "39",
    number = "16",
    pages = "2931-2936",
    month = "August",
    year = "2020",
    doi = "10.1021/acs.organomet.0c00519",
    issn = "0276-7333",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200810-142124575",
    note = "© 2020 American Chemical Society. \n\nPublished: August 10, 2020. \n\nWe thank the students from each of our groups for their invaluable advice and feedback as we wrote this Editorial, including Hanna Clements (U of Utah), Kristen Gardner (UC Berkeley), Shane Lies (UW Madison), and Brandon Wright (UC Berkeley). In addition, we are grateful to all of the students in our groups, who have taught us so much over the years about being better mentors. We are indebted to Prof. Brian Stoltz (Caltech) and Prof. F. Dean Toste (UC Berkeley) for their important contributions in the early stages of writing this Editorial. \n\nThis Editorial came about after significant private conversations among many of us in the organic chemistry community following the publication of the Hudlicky Perspective. After these discussions about the persistent, baseless premises, we realized that it would be important for members of our field to repudiate them. Although we are all rightfully proud that the science of organic chemistry has made revolutionary advances over the last three decades, we have not yet succeeded in uprooting our field’s problematic history of unhealthy, exclusionary practices. We view this moment as an opportunity to initiate substantive change. We must act to realize a more diverse, equitable, and inclusive culture in the field of organic chemistry. \n\nViews expressed in this editorial are those of the authors and not necessarily the views of the ACS. \n\nThis Editorial is jointly published in The Journal of Organic Chemistry, Organic Letters, ACS Central Science, and Organometallics.",
    revision_no = "15",
    abstract = "By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/104888,
    title ="Organic Chemistry: A Call to Action for Diversity and Inclusion",
    author = "Reisman, Sarah E. and Sarpong, Richmond",
    journal = "Journal of Organic Chemistry",
    volume = "85",
    number = "16",
    pages = "10287-10292",
    month = "August",
    year = "2020",
    doi = "10.1021/acs.joc.0c01607",
    issn = "0022-3263",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200810-134855232",
    note = "© 2020 American Chemical Society. \n\nPublished: August 10, 2020.\n\nWe thank the students from each of our groups for their invaluable advice and feedback as we wrote this Editorial, including Hanna Clements (U of Utah), Kristen Gardner (UC Berkeley), Shane Lies (UW Madison), and Brandon Wright (UC Berkeley). In addition, we are grateful to all of the students in our groups, who have taught us so much over the years about being better mentors. We are indebted to Prof. Brian Stoltz (Caltech) and Prof. F. Dean Toste (UC Berkeley) for their important contributions in the early stages of writing this Editorial. \n\nThis Editorial came about after significant private conversations among many of us in the organic chemistry community following the publication of the Hudlicky Perspective. After these discussions about the persistent, baseless premises, we realized that it would be important for members of our field to repudiate them. Although we are all rightfully proud that the science of organic chemistry has made revolutionary advances over the last three decades, we have not yet succeeded in uprooting our field’s problematic history of unhealthy, exclusionary practices. We view this moment as an opportunity to initiate substantive change. We must act to realize a more diverse, equitable, and inclusive culture in the field of organic chemistry. \n\nViews expressed in this editorial are those of the authors and not necessarily the views of the ACS. \n\nThis Editorial is jointly published in The Journal of Organic Chemistry, Organic Letters, ACS Central Science, and Organometallics.",
    revision_no = "15",
    abstract = "By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/104896,
    title ="Organic Chemistry: A Call to Action for Diversity and Inclusion",
    author = "Reisman, Sarah E. and Sarpong, Richmond",
    journal = "Organic Letters",
    volume = "22",
    number = "16",
    pages = "6223-6228",
    month = "August",
    year = "2020",
    doi = "10.1021/acs.orglett.0c02559",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200810-150113613",
    note = "© 2020 American Chemical Society.\n\nReceived 31 July 2020. Published online 10 August 2020. Published in issue 21 August 2020. \n\nWe thank the students from each of our groups for their invaluable advice and feedback as we wrote this Editorial, including Hanna Clements (U of Utah), Kristen Gardner (UC Berkeley), Shane Lies (UW Madison), and Brandon Wright (UC Berkeley). In addition, we are grateful to all of the students in our groups, who have taught us so much over the years about being better mentors. We are indebted to Prof. Brian Stoltz (Caltech) and Prof. F. Dean Toste (UC Berkeley) for their important contributions in the early stages of writing this Editorial. \n\nThis Editorial came about after significant private conversations among many of us in the organic chemistry community following the publication of the Hudlicky Perspective. After these discussions about the persistent, baseless premises, we realized that it would be important for members of our field to repudiate them. Although we are all rightfully proud that the science of organic chemistry has made revolutionary advances over the last three decades, we have not yet succeeded in uprooting our field’s problematic history of unhealthy, exclusionary practices. We view this moment as an opportunity to initiate substantive change. We must act to realize a more diverse, equitable, and inclusive culture in the field of organic chemistry. \n\nViews expressed in this editorial are those of the authors and not necessarily the views of the ACS. \n\nThis Editorial is jointly published in The Journal of Organic Chemistry, Organic Letters, ACS Central Science, and Organometallics.",
    revision_no = "12",
    abstract = "By now, most of us in the field of organic chemistry have become aware of the recent Perspective Article by Hudlicky published on the Angewandte Chemie, International Edition website(1) and then quickly removed as a result of rapid and strong denunciation on social media and in other forums. We have had complex emotional responses to the opinions expressed in this piece regarding the effects of diversity and inclusion efforts in chemistry: anger, that such regressive views were provided a platform in one of our leading chemistry journals; surprise, that the piece made it through the peer review process; and disappointment, that these views continue to persist, despite our hope that the climate for researchers in organic chemistry had improved since we were all trainees.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/106513,
    title ="Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)",
    author = "Hofstra, Julie L. and DeLano, Travis",
    journal = "Organic Syntheses",
    volume = "97",
    
    pages = "172-188",
    month = "August",
    year = "2020",
    doi = "10.15227/orgsyn.097.0172",
    issn = "2333-3553",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20201109-125642953",
    note = "© 2020 Organic Syntheses, Inc. \n\nPublished on the Web 8/20/2020. \n\nChecked by Sergio Cuesta-Galisteo, Jorge A. González, and Cristina Nevado.",
    revision_no = "8",
    abstract = "A. Bis((3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)methane (3) . An oven-dried 2-L three-necked, round-bottomed flask equipped with a 6.5 cm × 2.0 cm Teflon-coated elliptical stir bar is fitted with a thermometer, a reflux condenser and a rubber septum. The system is connected to a continuous nitrogen flow and then charged with (1R,2S)-(+)-cis-1-amino-2-indanol (1, 22.2 g, 149 mmol, 2.1 equiv), diethyl malonimidate dihydrochloride (2, 16.4 g, 71 mmol, 1 equiv), and 1 L of dichloromethane (Note 2). The system is heated to 45 °C (internal temperature 43 °C) under an atmosphere of nitrogen in an oil bath for 18 h, stirring at 600 rpm. Reaction progress is monitored by ¹H NMR (Note 3) (Figure 1).",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/104020,
    title ="Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions",
    author = "Poremba, Kelsey E. and Dibrell, Sara E.",
    journal = "ACS Catalysis",
    volume = "10",
    number = "15",
    pages = "8237-8246",
    month = "August",
    year = "2020",
    doi = "10.1021/acscatal.0c01842",
    issn = "2155-5435",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200624-154304037",
    note = "© 2020 American Chemical Society. \n\nReceived: April 24, 2020; Revised: June 19, 2020; Published: June 24, 2020. \n\nFellowship support was provided by the National Science Foundation (graduate research fellowship to K.E.P., S.E.D. Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "16",
    abstract = "Nickel-catalyzed reductive cross-coupling reactions have emerged as powerful methods to join two electrophiles. These reactions have proven particularly useful for the coupling of sec-alkyl electrophiles to form stereogenic centers; however, the development of enantioselective variants remains challenging. In this Perspective, we summarize the progress that has been made toward Ni-catalyzed enantioselective reductive cross-coupling reactions.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/103768,
    title ="Diversity-Oriented Enzymatic Synthesis of Cyclopropane Building Blocks",
    author = "Wittmann, Bruce J. and Knight, Anders M.",
    journal = "ACS Catalysis",
    volume = "10",
    number = "13",
    pages = "7112-7116",
    month = "July",
    year = "2020",
    doi = "10.1021/acscatal.0c01888",
    issn = "2155-5435",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200608-115355402",
    note = "© 2020 American Chemical Society. \n\nReceived: April 28, 2020; Revised: June 4, 2020; Published: June 4, 2020. \n\nThis work was supported by NSF MCB (grant 1513007 to F.H.A.), NSF STTR (grant 1738308 to F.H.A.), and the NIH (grant R35GM118191-01 to S.E.R.). Graduate student support from NIH T32 training grants GM112592 (A.M.K.) and GM07616 (B.J.W.), and the NSF Graduate Research Fellowship Program (A.M.K. and J.L.H., DGE-1144469), is acknowledged. The authors thank Mr. Lawrence M. Henling for assistance with small-molecule X-ray crystallography, as well as Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements. Crystallography experiments were supported by Jens Kaiser and the Caltech Molecular Observatory. The authors thank Jingzhou Wang for technical assistance, David Rozzell, Nathaniel Goldberg, Ferdinand Huber, Nicholas Porter, and Kari Hernandez for valuable discussions, and Sabine Brinkmann-Chen and Zhen Liu for critical reading of the manuscript. \n\nAuthor Contributions: B.J.W., A.M.K.: These authors contributed equally. The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. \n\nThe authors declare the following competing financial interest(s): A provisional patent, on which A.M.K., B.J.W., and S.B.J.K. are inventors, has been filed through the California Institute of Technology based on the results presented here.",
    revision_no = "23",
    abstract = "While biocatalysis is increasingly incorporated into drug development pipelines, it is less commonly used in the early stages of drug discovery. By engineering a protein to produce a chiral motif with a derivatizable functional handle, biocatalysts can be used to help generate diverse building blocks for drug discovery. Here we show the engineering of two variants of Rhodothermus marinus nitric oxide dioxygenase (RmaNOD) to catalyze the formation of cis- and trans-diastereomers of a pinacolboronate-substituted cyclopropane which can be readily derivatized to generate diverse stereopure cyclopropane building blocks.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/102000,
    title ="SeO₂-Mediated Oxidative Transposition of Pauson–Khand Products",
    author = "Dibrell, Sara E. and Maser, Michael R.",
    journal = "Journal of the American Chemical Society",
    volume = "142",
    number = "14",
    pages = "6483-6487",
    month = "April",
    year = "2020",
    doi = "10.1021/jacs.9b13818",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200319-125552181",
    note = "© 2020 American Chemical Society.  \n\nReceived: January 9, 2020; Published: March 19, 2020. \n\nWe thank Dr. M. Takase and L. Henling (both of Caltech) for X-ray data collection and Dr. J. Hofstra (Caltech) for X-ray data refinement. Dr. S. Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. Fellowship support was provided by the NSF (S.E.D., M.R.M. Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is acknowledged. \n\nAuthor Contributions: S.E.D. and M.R.R. contributed equally to this work. \n\nThe authors declare no competing financial interest. \n\nThe X-ray crystal structure data for compound 15e was submitted to the Cambridge Crystallographic Data Center, No. 1970101.",
    revision_no = "22",
    abstract = "Oxidative transpositions of bicyclic cyclopentenones mediated by selenium dioxide (SeO₂) are disclosed. Treatment of Pauson–Khand reaction (PKR) products with SeO₂ in the presence or absence of water furnishes di- and trioxidized cyclopentenones, respectively. Mechanistic investigations reveal multiple competing oxidation pathways that depend on substrate identity and water concentration. Functionalization of the oxidized products via cross-coupling methods demonstrates their synthetic utility. These transformations allow rapid access to oxidatively transposed cyclopentenones from simple PKR products.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/97642,
    title ="Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides",
    author = "Hofstra, Julie L. and Poremba, Kelsey E.",
    journal = "Angewandte Chemie International Edition",
    volume = "58",
    number = "42",
    pages = "14901-14905",
    month = "October",
    year = "2019",
    doi = "10.1002/anie.201906815",
    issn = "1433-7851",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190805-134105383",
    note = "© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. \n\nManuscript received: May 31, 2019; Revised manuscript received: August 9, 2019; Accepted manuscript online: August 13, 2019; Version of record online: September 19, 2019. \n\nWe thank the following Caltech staff for their help: Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to experimental and analytical equipment; Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements; and Dr. Paul Oyala for assistance with EPR experiments. We also thank Jordan C. Beck for assistance in the preparation of alkenyl triflates 1\u2009e and 1\u2009k. Fellowship support was provided by the National Science Foundation (graduate research fellowship to J.L.H. and K.E.P., Grant No. DGE‐1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191‐01) is gratefully acknowledged. \n\nThe authors declare no conflict of interest.",
    revision_no = "44",
    abstract = "A Ni‐catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench‐stable Ni(OAc)_2⋅4\u2009H_2O as a precatalyst and proceeds at room temperature in the presence of sub‐stoichiometric Zn and either 1,5‐cyclooctadiene or 4‐(N,N‐dimethylamino)pyridine.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/96224,
    title ="A 16-step synthesis of the isoryanodane diterpene (+)-perseanol",
    author = "Han, Arthur and Tao, Yujia",
    journal = "Nature",
    volume = "573",
    number = "7775",
    pages = "563-567",
    month = "September",
    year = "2019",
    doi = "10.1038/s41586-019-1580-x",
    issn = "0028-0836",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190610-080930538",
    note = "© 2019 Nature Publishing Group. \n\nReceived 09 May 2019; Accepted 15 July 2019; Published 25 September 2019. \n\nData availability: Characterization data for all compounds produced in this study are available in Supplementary Information or on request from the corresponding author. Metrical parameters for the structures of 32 and S21 are available free of charge from the Cambridge Crystallographic Data Centre (CCDC, https://www.ccdc.cam.ac.uk/) under reference numbers 1909375 and 1914686, respectively. \n\nWe acknowledge S. Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment; L. Henling and J. Hofstra for X-ray data collection and data refinement, respectively, for the structures of 32 and S21; Y. Zhang for providing original spectral data of perseanol; and K. Chuang for contributions to the synthetic design. Fellowship support was provided by the National Institutes of Health (NIH; Nos. 5T32GM007616-37 and 1F31GM120821, to A.H.). S.E.R. is a Heritage Medical Research Investigator. Financial support from the NIH (Nos. NIGMS RGM097582-01 and R35GM118191-01), Eli Lilly and Novartis is acknowledged. \n\nAuthor Contributions: A.H. and S.E.R. conceived this work; A.H., Y.T. and S.E.R. designed the experiments and analysed the data; A.H. and Y.T. conducted the experiments; and A.H. and S.E.R. wrote the manuscript. \n\nCompeting interests: The authors declare no competing interests. ",
    revision_no = "50",
    abstract = "(+)-Perseanol is an isoryanodane diterpene that is isolated from the tropical shrub Persea indica and has potent antifeedant and insecticidal properties. It is structurally related to (+)-ryanodine, which is a high-affinity ligand for and modulator of ryanodine receptors—ligand-gated ion channels that are critical for intracellular Ca^(2+) signalling in most multicellular organisms. Ryanodine itself modulates ryanodine-receptor-dependent Ca^(2+) release in many organisms, including mammals; however, preliminary data indicate that ryanodane and isoryanodane congeners that lack the pyrrole-2-carboxylate ester—such as perseanol—may have selective activity in insects. Here we report a chemical synthesis of (+)-perseanol, which proceeds in 16 steps from commercially available (R)-pulegone. The synthesis involves a two-step annulation process that rapidly assembles the tetracyclic core from readily accessible cyclopentyl building blocks. This work demonstrates how convergent fragment coupling, when combined with strategic oxidation tactics, can enable the concise synthesis of complex and highly oxidized diterpene natural products.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/96697,
    title ="Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis",
    author = "DeLano, Travis J. and Reisman, Sarah E.",
    journal = "ACS Catalysis",
    volume = "9",
    number = "8",
    pages = "6751-6754",
    month = "August",
    year = "2019",
    doi = "10.1021/acscatal.9b01785",
    issn = "2155-5435",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190625-112222475",
    note = "© 2019 American Chemical Society. \n\nReceived: May 1, 2019; Revised: June 21, 2019;\nPublished: June 25, 2019.\n\nWe thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank Dr. Julie Hofstra for assistance with experimental design. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, T.J.D., Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "22",
    abstract = "An electrochemically driven enantioselective nickel-catalyzed reductive cross-coupling of alkenyl bromides and benzyl chlorides is reported. The reaction forms products bearing allylic stereogenic centers with good enantioselectivity under mild conditions in an undivided cell. Electrochemical activation and turnover of the catalyst mitigate issues posed by metal powder reductants. This report demonstrates that enantioselective Ni-catalyzed cross-electrophile couplings can be driven electrochemically.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/92078,
    title ="A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A",
    author = "Beck, Jordan C. and Lacker, Caitlin R.",
    journal = "Chemical Science",
    volume = "10",
    number = "8",
    pages = "2315-2319",
    month = "February",
    year = "2019",
    doi = "10.1039/c8sc05444d",
    issn = "2041-6520",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190104-074958444",
    note = "© The Royal Society of Chemistry 2018. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. \n\nReceived 6th December 2018. Accepted 19th December 2018. \n\nWe thank Dr Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Fellowship support was provided by an NIH Training Grant (J. C. B., Grant No. 5T32GM007616-39) and the NSF (C. R. L. and L. M. C., Grant No. DGE-1144469) and. S. E. R. is a Heritage Medical Research Foundation Investigator. Partial financial support from the NSF (CAREER-1057143) and NIH (R35GM118191-01), as well as the Research Corporation Cottrell Scholars program, is gratefully acknowledged. \n\nConflicts of interest: There are no conflicts to declare. \n\nAll publication charges for this article have been paid for by the Royal Society of Chemistry.",
    revision_no = "36",
    abstract = "A modular synthesis of enantioenriched polyfunctionalized cyclobutanes was developed that features an 8-aminoquinolinamide directed C–H arylation reaction. The C–H arylation products were derivatized through subsequent decarboxylative coupling processes. This synthetic strategy enabled a 9-step enantioselective total synthesis of the antiproliferative meroterpenoid (+)-rumphellaone A.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/92452,
    title ="Organic Letters 2.0: A New Beginning",
    author = "Carreira, Erick M. and Brimble, Margaret",
    journal = "Organic Letters",
    volume = "21",
    number = "1",
    pages = "1-4",
    month = "January",
    year = "2019",
    doi = "10.1021/acs.orglett.8b03964",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190124-111248679",
    note = "© 2019 American Chemical Society. \n\nReceived: December 12, 2018; Published: January 4, 2019.",
    revision_no = "11",
    abstract = "Last year, Organic Letters celebrated its 20-year anniversary. To younger authors and readers, it is hard to appreciate that Organic Letters, as the new kid on the block back then as far as ACS journals go, was trail-blazing in its approach to all aspects of scientific publications—a letters journal that rapidly published top-shelf, rigorously peer-reviewed research. It is hard to believe now that two decades have elapsed since the journal’s launch with Professor Amos B. Smith III as the founding Editor-in-Chief. Under Prof. Smith’s visionary, steady leadership, Organic Letters quickly skyrocketed to the preeminent position it holds today as the leading organic chemistry journal. Organic Letters has benefitted from a close-knit group of Associate Editors that enjoys the broad respect of the community at large, because they are active scientists engaged in all aspects of research, including publication of high-caliber science. This is reassuring to scientists—authors who entrust their hard work to the rigors of peer review.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/88374,
    title ="Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides",
    author = "Su, Justin Y. and Grünenfelder, Denise C.",
    journal = "Organic Letters",
    volume = "20",
    number = "16",
    pages = "4912-4916",
    month = "August",
    year = "2018",
    doi = "10.1021/acs.orglett.8b02045",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20180731-110815223",
    note = "© 2018 American Chemical Society. \n\nReceived: June 29, 2018; Published: July 31, 2018. \n\nWe thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Nicholas J. Fastuca for assistance in substrate preparation and Dr. Matthew J. Hesse for helpful discussions (both of Caltech). Fellowship support was provided by the National Science Foundation (graduate research fellowship to D.C.G., Grant No. DGE-1144469). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NSF (CAREER-1057143) is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "20",
    abstract = "A radical deoxychlorination of cesium oxalates has been developed for the preparation of hindered secondary and tertiary alkyl chlorides. The reaction tolerates a number of functional groups, including ketones, alcohols, and amides, and provides complementary reactivity to standard deoxychlorination reactions proceeding by heterolytic mechanisms. Preliminary studies demonstrate that the developed conditions can also be applied to deoxybromination and deoxyfluorination reactions.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/87056,
    title ="An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol",
    author = "Xu, Chen and Han, Arthur",
    journal = "Organic Letters",
    volume = "20",
    number = "13",
    pages = "3793-3796",
    month = "July",
    year = "2018",
    doi = "10.1021/acs.orglett.8b01387",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20180613-100330914",
    note = "© 2018 American Chemical Society. \n\nReceived: May 2, 2018; Published: June 13, 2018. \n\nAccession Codes: CCDC 1840855 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033. \n\nWe thank Dr. Michael Takase and Larry Henling (both of Caltech) for X-ray data collection and Ms. Julie Hofstra (Caltech) for X-ray data refinement. Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. Fellowship support was provided by the Shenzhen UV-ChemTech Inc. (C.X.), and the NIH (A.H., Nos. 5T32GM007616-37 and 1F31GM120821). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (Nos. NIGMS RGM097582-01 and R35GM118191-01), Eli Lilly, and Novartis is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "24",
    abstract = "An approach to synthesize the pentacyclic framework of the polyol diterpenoid ryanodol is reported. The ABC tricycle was constructed by a Co-mediated Pauson–Khand reaction, and both radical and anionic cyclization pathways were developed to form the E-ring. In addition, a reaction sequence involving SeO_2-mediated enone oxidation and hydroxyl-directed oxy-Michael addition was developed to introduce the A-ring oxidation. The feasibility of forming the bridging D-ring by an oxidative dearomatization was established.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/86239,
    title ="Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B",
    author = "Chapman, Lauren M. and Beck, Jordan C.",
    journal = "Journal of Organic Chemistry",
    volume = "83",
    number = "11",
    pages = "6066-6085",
    month = "June",
    year = "2018",
    doi = "10.1021/acs.joc.8b00728",
    issn = "0022-3263",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20180507-092121998",
    note = "© 2018 American Chemical Society. \n\nReceived: March 22, 2018; Published: May 4, 2018. \n\nProf. Greg Fu is gratefully acknowledged for insightful discussions. We thank Dr. Allen Oliver, Dr. Nathan Schley, and Ms. Julie Hofstra for X-ray crystallographic structure determination and Dr. David VanderVelde for assistance with NMR structure determination. We thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Materia, Inc. for a donation of HG-II catalyst. Fellowship support was provided by the NSF (L.M.C. and C.R.L., Grant No. DGE-1144469), NIH Training Grant (J.C.B., Grant No. 5T32GM007616-39) and SNF (L.W., Grant No. PBZHP2-147311). S.E.R. is an American Cancer Society Research Scholar and a Heritage Medical Research Foundation Investigator. Financial support from the NSF (CAREER-1057143), the American Cancer Society, the Research Corporation Cottrell Scholars program, and DuPont is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "28",
    abstract = "(+)-Psiguadial B is a diformyl phloroglucinol meroterpenoid that exhibits antiproliferative activity against the HepG2 human hepatoma cancer cell line. This full account details the evolution of a strategy that culminated in the first enantioselective total synthesis of (+)-psiguadial B. A key feature of the synthesis is the construction of the trans-cyclobutane motif by a Wolff rearrangement with in situ catalytic, asymmetric trapping of the ketene. An investigation of the substrate scope of this method to prepare enantioenriched 8-aminoquinolinamides is disclosed. Three routes toward (+)-psiguadial B were evaluated that featured the following key steps: (1) an ortho-quinone methide hetero-Diels–Alder cycloaddition to prepare the chroman framework, (2) a Prins cyclization to form the bridging bicyclo[4.3.1]decane system, and (3) a modified Norrish–Yang cyclization to generate the chroman. Ultimately, the successful strategy employed a ring-closing metathesis to form the seven-membered ring and an intramolecular O-arylation reaction to complete the polycyclic framework of the natural product.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/84305,
    title ="Total Synthesis of (+)-Pleuromutilin",
    author = "Farney, Elliot P. and Feng, Sean S.",
    journal = "Journal of the American Chemical Society",
    volume = "140",
    number = "4",
    pages = "1267-1270",
    month = "January",
    year = "2018",
    doi = "10.1021/jacs.7b13260",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20180112-131323403",
    note = "© 2018 American Chemical Society. \n\nReceived: December 15, 2017; Published: January 11, 2018. \n\nWe thank Dr. Michael Takase and Larry Henling for X-ray data collection, Ms. Julie Hofstra for X-ray data refinement, Dr. David VanderVelde for assistance with NMR structure determination, Dr. Scott Virgil for assistance with crystallization of 26, and the Caltech 3CS for access to analytical equipment. Fellowship support was provided by the NIH (E.P.F., Grant 1F32GM117764) and NSF (S.S.F., DGE-1144469). Financial support from the Heritage Medical Research Institute is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "32",
    abstract = "An 18-step synthesis of the antibiotic (+)-pleuromutilin is disclosed. The key steps of the synthesis include a highly stereoselective SmI2-mediated cyclization to establish the eight-membered ring and a stereospecific transannular [1,5]-hydrogen atom transfer to set the C10 stereocenter. This strategy was also used to prepare (+)-12-epi-pleuromutilin. The chemistry described here will enable efforts to prepare new mutilin antibiotics.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/83692,
    title ="Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling",
    author = "Hofstra, Julie L. and Cherney, Alan H.",
    journal = "Journal of the American Chemical Society",
    volume = "140",
    number = "1",
    pages = "139-142",
    month = "January",
    year = "2018",
    doi = "10.1021/jacs.7b11707",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20171205-112031343",
    note = "© 2017 American Chemical Society.\n\nReceived: November 3, 2017. Published: December 4, 2017. \n\nWe thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Dr. Michael K. Takase and Mr. Lawrence M. Henling for assistance with X-ray crystallography, as well as Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, J.L.H., A.H.C., Grant No. DGE-1144469) and Caltech SURF program (Richard H. Cox and John Stauffer Fellowships, C.M.O.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01; GM111805-01) is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "31",
    abstract = "An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75016,
    title ="Chemical Synthesis of (+)-Ryanodine and (+)-20-Deoxyspiganthine",
    author = "Xu, Chen and Han, Arthur",
    journal = "ACS Central Science",
    volume = "3",
    number = "4",
    pages = "278-282",
    month = "April",
    year = "2017",
    doi = "10.1021/acscentsci.6b00361",
    issn = "2374-7943",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170310-084018084",
    note = "© 2017 American Chemical Society. ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. \n\nReceived: November 22, 2016;\nPublished: March 9, 2017.\n\nThe Caltech Center for Catalysis and Chemical Synthesis is gratefully acknowledged for access to analytical equipment. We thank Dr. Michael Takase and Larry Henling for acquiring the X-ray diffraction data and Julie Hofstra for solving the structures of compounds 1, 3, 16, and 18. Fellowship support was provided by the Shenzhen UV-ChemTech Inc. (postdoctoral fellowship to C.X.) and the NIH (training grant 5T32GM007616-37 to A.H.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute investigator. Financial support from the NIH (NIGMS RGM097582-01, R35GM118191-01), Eli Lilly, and Novartis is gratefully acknowledged.",
    revision_no = "25",
    abstract = "(+)-Ryanodine is a natural product modulator of ryanodine receptors, important intracellular calcium ion channels that play a critical role in signal transduction leading to muscle movement and synaptic transmission. Chemical derivatization of (+)-ryanodine has demonstrated that certain peripheral structural modifications can alter its pharmacology, and that the pyrrole-2-carboxylate ester is critical for high affinity binding to ryanodine receptors. However, the structural variation of available ryanodine analogues has been limited by the challenge of site-specific functionalization of semisynthetic intermediates, such as (+)-ryanodol. Here we report a synthetic strategy that provides access to (+)-ryanodine and the related natural product (+)-20-deoxyspiganthine in 18 and 19 steps, respectively. A key feature of this strategy is the reductive cyclization of an epoxide intermediate that possesses the critical pyrrole-2-carboxylate ester. This approach allows for the direct introduction of this ester in the final stage of the synthesis and provides a framework for the synthesis of previously inaccessible synthetic ryanoids.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/76561,
    title ="Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes",
    author = "Poremba, Kelsey E. and Kadunce, Nathaniel T.",
    journal = "Journal of the American Chemical Society",
    volume = "139",
    number = "16",
    pages = "5684-5687",
    month = "April",
    year = "2017",
    doi = "10.1021/jacs.7b01705",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170414-064225830",
    note = "© 2017 American Chemical Society. \n\nReceived 17 February 2017. Published online 13 April 2017. \n\nWe are grateful to Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank Dr. Leah Cleary for the initial preparation of ligands and Julie Hofstra for solving the structure of 3k (CCDC Deposition No. 1533022). Fellowship support was provided by the National Science Foundation (graduate research fellowship to K. E. P., Grant No. DGE-1144469), Amgen (Graduate Research Fellowship to N.T.K.), and Shionogi & Co., Ltd. (fellowship to N.S.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (NIGMS R35GM118191-01; GM111805-01) is gratefully acknowledged.",
    revision_no = "41",
    abstract = "An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, indoles, and piperidines.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75732,
    title ="Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides",
    author = "Suzuki, Naoyuki and Hofstra, Julie L.",
    journal = "Organic Letters",
    volume = "19",
    number = "8",
    pages = "2150-2153",
    month = "April",
    year = "2017",
    doi = "10.1021/acs.orglett.7b00793",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170405-103159884",
    note = "© 2017 American Chemical Society. \n\nReceived: March 16, 2017; Published: April 4, 2017. \n\nWe thank the following Caltech staff for their help: Dr. Scott Virgil of the Caltech Center for Catalysis and Chemical Synthesis for access to experimental and analytical equipment; Dr. Michael K. Takase and Larry M. Henling for assistance in collecting X-ray diffraction data; and Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements. We also thank Kevin Sokol and Dr. Alan Cherney (both of Caltech) for preparing NHP esters 6g and 6h and vinyl bromides 1g, 1h, and 1l, respectively. Fellowship support was provided by the National Science Foundation (graduate research fellowship to J.L.H. and K.E.P., Grant No. DGE-1144469) and Shionogi & Co., Ltd. (postdoctoral fellowship to N.S.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (NIGMS RGM097582-01, R35GM118191) is gratefully acknowledged. \n\nN.S. and J.L.H. contributed equally to this work. \n\nThe authors declare no competing financial interest.",
    revision_no = "27",
    abstract = "An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75505,
    title ="Enantioselective Synthesis of (−)-Acetylapoaranotin",
    author = "Wang, Haoxuan and Regan, Clinton J.",
    journal = "Organic Letters",
    volume = "19",
    number = "7",
    pages = "1698-1701",
    month = "April",
    year = "2017",
    doi = "10.1021/acs.orglett.7b00418",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170329-093225716",
    note = "© 2017 American Chemical Society. ACS Editors' Choice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. \n\nReceived: February 17, 2017; Published: March 28, 2017. \n\nWe gratefully acknowledge Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Dr. David VanderVelde for assistance with NMR structure analysis. We thank Materia, Inc. and Sigma-Aldrich for donations of chemicals. We also thank Amy McCarthy, Geanna Min, and Madeleine Kieffer of Caltech for the preparation of synthetic intermediates. Fellowship support was provided by the Department of Defense (DoD) through the National Defense Science & Engineering Graduate Fellowship Program (J.A.C.), the NSF Graduate Research Fellowship Program (J.A.C., Grant No. DGE-0703267), and the Swiss National Science Foundation (P.R.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute investigator. Financial support from the NIH (NIGMS RGM097582A), the American Cancer Society, the Research Corporation Cottrell Scholar program, and DuPont is gratefully acknowledged.",
    revision_no = "22",
    abstract = "The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (−)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (−)-emethallicin E and (−)-haemotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/70275,
    title ="A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans",
    author = "Chuang, Kangway V. and Kieffer, Madeleine E.",
    journal = "Organic Letters",
    volume = "18",
    number = "18",
    pages = "4750-4753",
    month = "September",
    year = "2016",
    doi = "10.1021/acs.orglett.6b02477",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20160912-094332366",
    note = "© 2016 American Chemical Society. \n\nReceived: August 18, 2016; Publication Date (Web): September 6, 2016. \n\nWe thank Dr. Scott Virgil of Caltech for helpful discussions, the Caltech Center for Catalysis and Chemical Synthesis for access to screening facilities and analytical equipment, and Sigma–Aldrich for a kind donation of chemicals. We gratefully acknowledge Jordan Beck and Lauren Chapman of Caltech for their assistance in the preparation of this manuscript. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship to M.E.K. and K.V.C., Grant No. DGE-1144469). S.E.R. is an American Cancer Society Research Scholar and a Heritage Medical Research Foundation investigator. Financial support from the NIH (NIGMS RGM097582A) and the donors of the ACS Petroleum Research Foundation is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "25",
    abstract = "A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P(^tBu)_3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent total synthesis of the bisindole natural product (−)-aspergilazine A.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/68795,
    title ="A 15-step synthesis of (+)-ryanodol",
    author = "Chuang, Kangway V. and Xu, Chen",
    journal = "Science",
    volume = "353",
    number = "6302",
    pages = "912-915",
    month = "August",
    year = "2016",
    doi = "10.1126/science.aag1028",
    issn = "0036-8075",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20160630-153826956",
    note = "© 2016 American Association for the Advancement of Science. \n\n9 May 2016; accepted 25 July 2016. \n\nThe California Institute of Technology Center for Catalysis and Chemical Synthesis is gratefully acknowledged for access to analytical equipment. We thank S. Virgil and J. Hofstra for assistance in obtaining x-ray–quality crystals and solving the structure of 15, respectively. M. Takase and L. Henling are acknowledged for acquiring the x-ray diffraction data for 15 (CCDC deposition no. 1478621; the data are available free of charge from The Cambridge Crystallographic Data Centre). M. Kieffer is gratefully acknowledged for critical feedback and helpful suggestions. Fellowship support was provided by the National Science Foundation (graduate research fellowship to K.V.C., grant DGE-1144469) and the Shenzhen UV-ChemTech Inc. (postdoctoral fellowship to C.X.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute investigator. Financial support from the NIH (National Institute of General Medical Sciences grant RGM097582-01), Eli Lilly, and Novartis is gratefully acknowledged. The California Institute of Technology has filed a provisional patent on this work (application no. 62/269,760).",
    revision_no = "31",
    abstract = "(+)-Ryanodine and (+)-ryanodol are complex diterpenoids that modulate intracellular calcium-ion release at ryanodine receptors, ion channels critical for skeletal and cardiac muscle excitation-contraction coupling and synaptic transmission. Chemical derivatization of these diterpenoids has demonstrated that certain peripheral structural modifications can alter binding affinity and selectivity among ryanodine receptor isoforms. Here, we report a short chemical synthesis of (+)-ryanodol that proceeds in only 15 steps from the commercially available terpene (S)-pulegone. The efficiency of the synthesis derives from the use of a Pauson-Khand reaction to rapidly build the carbon framework and a SeO_2-mediated oxidation to install three oxygen atoms in a single step. This work highlights how strategic C–O bond constructions can streamline the synthesis of polyhydroxylated terpenes by minimizing protecting group and redox adjustments.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/69632,
    title ="Enantioselective Total Synthesis of (+)-Psiguadial B",
    author = "Chapman, Lauren M. and Beck, Jordan C.",
    journal = "Journal of the American Chemical Society",
    volume = "138",
    number = "31",
    pages = "9803-9806",
    month = "August",
    year = "2016",
    doi = "10.1021/jacs.6b07229",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20160815-142455841",
    note = "© 2016 American Chemical Society. \n\nReceived: July 13, 2016. Published: July 24, 2016. \n\nProf. Greg Fu is gratefully acknowledged for insightful discussions. We thank Dr. Allen Oliver and Dr. Nathan Schley for X-ray crystallographic structure determination, Dr. David VanderVelde for assistance with NMR structure determination, Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Materia, Inc. for a donation of HG-II catalyst. Fellowship support was provided by the NSF (L.M.C., Grant DGE-1144469) and SNF (L.W., Grant PBZHP2-147311). S.E.R. is an American Cancer Society Research Scholar and a Heritage Medical Research Foundation Investigator. Financial support from the California Institute of Technology, the NSF (CHE 1057143), the American Cancer Society, the Research Corporation Cottrell Scholars Program, and DuPont is gratefully acknowledged.",
    revision_no = "17",
    abstract = "The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp^3)–H alkenylation reaction to strategically forge the C1–C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/64312,
    title ="Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza-Prins Cascade Reaction",
    author = "Daniels, Blake E. and Ni, Jane",
    journal = "Angewandte Chemie International Edition",
    volume = "55",
    number = "10",
    pages = "3398-3402",
    month = "March",
    year = "2016",
    doi = "10.1002/ange.201510972View",
    issn = "1433-7851",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20160208-143917247",
    note = "© 2016 John Wiley & Sons, Inc. \n\nReceived: November 26, 2015. Published online: February 4, 2016. \n\nFunded by: National Institutes of Health. Grant Number: RR027690; NSERC; American Cancer Society Research Scholar; NIH, Grant Number: RGM097582A; American Chemical Society PRF.",
    revision_no = "20",
    abstract = "A conjugate addition/asymmetric protonation/aza-Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl_4 and 3,3′-dibromo-BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6-dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl_4⋅BINOL complex serves as a chiral Lewis-acid-assisted Brønsted acid.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/59772,
    title ="Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds",
    author = "Cherney, Alan H. and Kadunce, Nathaniel T.",
    journal = "Chemical Reviews",
    volume = "115",
    number = "17",
    pages = "9587-9652",
    month = "September",
    year = "2015",
    doi = "10.1021/acs.chemrev.5b00162",
    issn = "0009-2665",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20150819-143512446",
    note = "© 2015 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. \n\nReceived: March 17, 2015; Publication Date (Web): August 13, 2015. \n\nWe are grateful for financial support from the National Institutes of Health (Grant GM111805-01), Novartis, and Eli Lilly. Fellowship support from Bristol-Myers Squibb (A.H.C.), the American Chemical Society Division of Organic Chemistry, with sponsorship by Amgen (A.H.C.), and the National Science Foundation (A.H.C., Grant No. DGE-1144469) is gratefully acknowledged.",
    revision_no = "23",
    abstract = "The stereocontrolled construction of C−C bonds remains one of the foremost challenges in organic synthesis. At the heart of any chemical synthesis of a natural product or designed small molecule is the need to orchestrate a series of chemical reactions to prepare and functionalize a carbon framework. The advent of transition-metal catalysis has provided chemists with a broad range of new tools to forge C−C bonds and has resulted in a paradigm shift in synthetic strategy planning. The impact of these methods was recognized with the awarding of the 2010 Nobel Prize in Chemistry to Richard Heck, Ei-ichi Negishi, and Akira Suzuki for their seminal contributions to the development of Pd-catalyzed cross-coupling.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/60304,
    title ="Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles",
    author = "Kadunce, Nathaniel T. and Reisman, Sarah E.",
    journal = "Journal of the American Chemical Society",
    volume = "137",
    number = "33",
    pages = "10480-10483",
    month = "August",
    year = "2015",
    doi = "10.1021/jacs.5b06466",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20150917-141844097",
    note = "© 2015 American Chemical Society.\n\nReceived: June 22, 2015; Published: August 9, 2015.\n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Dr. Alan Cherney and Robert Scanes for helpful discussions, and Dr. Michael Takase and Julie Hofstra for X-ray crystallographic structure determination. S.E.R. is a Camille Dreyfus Teacher-Scholar and an American Cancer Society Research Scholar. Financial support from NIH (GM111805-01), Amgen, Novartis, and Eli Lilly is gratefully acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "22",
    abstract = "A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/58741,
    title ="A cationic cysteine-hydrazide as an enrichment tool for the mass spectrometric characterization of bacterial free oligosaccharides",
    author = "Jang, Kyoung-Soon and Nani, Roger R.",
    journal = "Analytical and Bioanalytical Chemistry",
    volume = "407",
    number = "20",
    pages = "6181-6190",
    month = "August",
    year = "2015",
    doi = "10.1007/s00216-015-8798-8",
    issn = "1618-2642",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20150701-133700441",
    note = "© 2015 Springer-Verlag Heidelberg.\n\nReceived: 3 February 2015; revised: 7 May 2015; accepted: 21 May 2015.\n\nWe thank Sarkis Mazmanian (Caltech) for providing support for bacterial culture growth. This work was supported by a Searle Scholar Fellowship and a Burroughs-Wellcome Fund Career Award to WMC. The Proteome Exploration Laboratory is  supported by the Gordon and Betty Moore Foundation through Grant GBMF775 and the Beckman Institute.",
    revision_no = "20",
    abstract = "In Campylobacterales and related ε-proteobacteria with N-linked glycosylation (NLG) pathways, free oligosaccharides (fOS) are released into the periplasmic space from lipid-linked precursors by the bacterial oligosaccharyltransferase (PglB). This hydrolysis results in the same molecular structure as the oligosaccharide that is transferred to a protein to be glycosylated. This allowed for the general elucidation of the fOS-branched structures and monosaccharides from a number of species using standard enrichment and mass spectrometry methods. To aid characterization of fOS, hydrazide chemistry has often been used for chemical modification of the reducing part of oligosaccharides resulting in better selectivity and sensitivity in mass spectrometry; however, the removal of the unreacted reagents used for the modification often causes the loss of the sample. Here, we develop a more robust method for fOS purification and characterize glycostructures using complementary tandem mass spectrometry (MS/MS) analysis. A cationic cysteine hydrazide derivative was synthesized to selectively isolate fOS from periplasmic fractions of bacteria. The cysteine hydrazide nicotinamide (Cyhn) probe possesses both thiol and cationic moieties. The former enables reversible conjugation to a thiol-activated solid support, while the latter improves the ionization signal during MS analysis. This enrichment was validated on the well-studied Campylobacter jejuni by identifying fOS from the periplasmic extracts. Using complementary MS/MS analysis, we approximated data of a known structure of the fOS from Campylobacter concisus. This versatile enrichment technique allows for the exploration of a diversity of protein glycosylation pathways.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/56462,
    title ="From alkaloids to terpenoids: New strategies and tactics for the synthesis of polycyclic natural products",
    author = "Reisman, Sarah E.",
    journal = "Abstracts of Papers of the American Chemical Society",
    volume = "249",
    
    pages = "ORGN-219",
    month = "March",
    year = "2015",
    
    issn = "0065-7727",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20150408-081804123",
    note = "© 2015 American Chemical Society.",
    revision_no = "10",
    abstract = "The chem. synthesis of natural products provides an exciting platform from which to conduct fundamental\nresearch in chem. and biol. Our lab. has ongoing research programs targeting the chem. syntheses of several\nnatural products, including members of the epidithiodiketopiperazines, the ent-kauranoids, and the acutumine\nalkaloids. The densely packed arrays of heteroatoms and stereogenic centers that constitute these polycyclic\ntargets challenge the limits of current technol. and inspire the development of new synthetic strategies and\ntactics. This seminar will describe our latest progress in both our methodol. and target-directed synthesis\nendeavors.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/50246,
    title ="Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles",
    author = "Cherney, Alan H. and Reisman, Sarah E.",
    journal = "Journal of the American Chemical Society",
    volume = "136",
    number = "41",
    pages = "14365-14368",
    month = "October",
    year = "2014",
    doi = "10.1021/ja508067c",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20141007-155137202",
    note = "© 2014 American Chemical Society. ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. \n\nReceived: August 6, 2014. Publication Date (Web): September 22, 2014. \n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech\nCenter for Catalysis and Chemical Synthesis for access to\nanalytical equipment. Fellowship support was provided by the\nNational Science Foundation (Graduate Research Fellowship,\nA.H.C., grant no. DGE-1144469) and the ACS Division of\nOrganic Chemistry (A.H.C., sponsored by Amgen). S.E.R. is a\nfellow of the Alfred P. Sloan Foundation, a Camille Dreyfus\nTeacher-Scholar, and an American Cancer Society Research\nScholar. Financial support from NIH (GM111805-01), Amgen,\nNovartis, DuPont, and Eli Lilly is gratefully acknowledged.",
    revision_no = "25",
    abstract = "A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/47494,
    title ="A unified strategy for the synthesis of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E",
    author = "Yeoman, John T. S. and Cha, Jacob Y.",
    journal = "Tetrahedron",
    volume = "70",
    number = "27-28",
    pages = "4070-4088",
    month = "July",
    year = "2014",
    doi = "10.1016/j.tet.2014.03.071 ",
    issn = "0040-4020",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20140725-092716157",
    note = "© 2014 Elsevier Ltd. \n\nReceived 19 February 2014; Received in revised form 17 March 2014; Accepted 21 March 2014; Available online 29 March 2014. \n\nWe thank Mr. Larry Henling and the late Dr. Michael Day for X-ray crystallographic structure determination and Dr. David VanderVelde for assistance with NMR structure determination. We also thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, as well as Sigmae-Aldrich for a kind donation of chemicals. The Bruker KAPPA APEXII X-ray diffractometer was purchased through an award to the California Institute of Technology by the NSF CRIF program (CHE-0639094). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Fellowship support from Bristol-Myers Squibb (_100002491) (J.T.S.Y.) and the National Science Foundation (_100000001) (Graduate Research Fellowship, V.W.M., Grant No. DGE-1144469) and financial support from the California Institute of Technology, the National Science Foundation (CAREER-1057143), Boehringer Ingelheim (_100001003), and Amgen (_100002429) are gratefully acknowledged.",
    revision_no = "15",
    abstract = "Herein we describe in full our investigations that led to the completion of the first total syntheses of (−)-maoecrystal Z, (−)-trichorabdal A, and (−)-longikaurin E. The unified strategy employs a Ti^(III)-mediated reductive epoxide coupling to rapidly prepare a key spirolactone. Highly diastereoselective Sm^(II)-mediated reductive cyclizations and a Pd^(II)-mediated oxidative cyclization enable the construction of three architecturally distinct ent-kauranoid frameworks from this common intermediate.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/45476,
    title ="Enantioselective Total Synthesis of (-)-Lansai B and (+)-Nocardioazines A and B",
    author = "Wang, Haoxuan and Reisman, Sarah E.",
    journal = "Angewandte Chemie International Edition",
    volume = "53",
    number = "24",
    pages = "6206-6210",
    month = "June",
    year = "2014",
    doi = "10.1002/anie.201402571",
    issn = "1433-7851",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20140505-085817109",
    note = "© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. \n\nArticle first published online: 28 Apr. 2014. \n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, as well as Materia, Inc. and Sigma–Aldrich for kind donations of chemicals. We are grateful to Dr. David VanderVelde for assistance with NMR structure analysis, and Mr. Larry Henling for X-ray structure determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased with an NSF Chemistry Research Instrumentation award to Caltech (CHE-0639094). NMR spectra were obtained on a spectrometer funded by the NIH (RR027690). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Financial support from the California Institute of Technology, the NIH (NIGMS RGM097582A, and DuPont is gratefully acknowledged.",
    revision_no = "21",
    abstract = "The concise total syntheses of the bis(pyrroloindolines) (−)-lansai B and (+)- nocardioazines A and B are reported. The key pyrroloindoline building blocks are rapidly prepared by enantioselective formal [3+2] cycloaddition reactions. The macrocycle of (+)-nocardioazine A is constructed by an unusual intramolecular diketopiperazine formation.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/43334,
    title ="Pd-catalyzed Fukuyama cross-coupling of secondary organozinc\nreagents for the direct synthesis of unsymmetrical ketones",
    author = "Cherney, Alan H. and Reisman, Sarah E.",
    journal = "Tetrahedron",
    volume = "70",
    number = "20",
    pages = "3259-3265",
    month = "May",
    year = "2014",
    doi = "10.1016/j.tet.2013.11.104",
    issn = "0040-4020",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20140113-100609164",
    note = "© 2013 Elsevier Ltd. \n\nReceived 26 August 2013. Received in revised form 21 November 2013. Accepted 29 November 2013.\nAvailable online 7 December 2013. \n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical\nequipment. We also thank Sigma-Aldrich for a kind donation of chemicals. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, A.H.C., Grant No. DGE-1144469). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Financial support from the California Institute of\nTechnology, Amgen, DuPont, Novartis, Boehringer Ingelheim, and the National Science Foundation (CAREER-1057143) is gratefully acknowledged.",
    revision_no = "23",
    abstract = "The coupling of acyl electrophiles with organometallic reagents represents a convergent route toward complex and versatile ketone products. Despite the mild conditions and high functional group tolerance, the cross-coupling of carboxylic acid derivatives, such as thioesters, and secondary organometallic reagents is an underdeveloped transformation. Herein, we disclose a convenient and efficient protocol for the Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents with thioester electrophiles. Under these mild conditions, a range of thioesters possessing sensitive functional groups can be coupled with either activated or unactivated secondary organozinc halides in good yields. This method was expanded to include an acid chloride substrate, generating an aryl alkyl ketone in high yield. In addition, a modest dynamic kinetic resolution of the organozinc reagent can be achieved using chiral phosphoramidite ligands to furnish enantioenriched ketone products.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/42921,
    title ="Recent Developments in the Catalytic, Asymmetric Construction of Pyrroloindolines Bearing All-Carbon Quaternary Stereocenters",
    author = "Repka, Lindsay M. and Reisman, Sarah E.",
    journal = "Journal of Organic Chemistry",
    volume = "78",
    number = "24",
    pages = "12314-12320",
    month = "December",
    year = "2013",
    doi = "10.1021/jo4017953",
    issn = "0022-3263",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20131210-103918595",
    note = "© 2013 American Chemical Society.\nReceived: August 15, 2013.\nPublication Date: December 2, 2013.\n\nWe thank the California Institute of Technology, the NIH\n(NIGMS RGM097582A), the Baxter Foundation, Amgen,\nBoehringer Ingelheim, and the donors of the ACS Petroleum\nResearch Foundation for providing financial support for our\nresearch efforts in this field. S.E.R. is a fellow of the Alfred P.\nSloan Foundation, a Camille Dreyfus Teacher−Scholar, and an\nAmerican Cancer Society Research Scholar. L.M.R was\nsupported by a fellowship from the ACS Division of Organic\nChemistry sponsored by Genentech.",
    revision_no = "21",
    abstract = "Pyrroloindoline alkaloids constitute a large family of natural products that\nhas inspired the development of an impressive array of new reactions to prepare the key\nheterocyclic motif. This synopsis will address catalytic, asymmetric reactions developed to\nsynthesize pyrroloindolines bearing C3a all-carbon quaternary stereocenters. The\nmethods described herein include both transition-metal-catalyzed and organocatalyzed\nreactions that have been demonstrated to be suitable for the synthesis of the\npyrroloindoline framework.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/42857,
    title ="Microbiota Modulate Behavioral and Physiological Abnormalities Associated with Neurodevelopmental Disorders",
    author = "Hsiao, Elaine Y. and McBride, Sara W.",
    journal = "Cell",
    volume = "155",
    number = "7",
    pages = "1451-1463",
    month = "December",
    year = "2013",
    doi = "10.1016/j.cell.2013.11.024",
    issn = "0092-8674",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20131205-105756544",
    note = "© 2013 Elsevier Inc. \n\nReceived: August 20, 2013; Revised: October 3, 2013; Accepted: November 18, 2013; Published: December 5, 2013. \n\nWe acknowledge Reyna Sauza, Jaime Rodriguez, and Taren Thron for caring for the animals; Dr. Michael Fischbach (UCSF) for advising on pathways of 4EPS and indolepyruvate synthesis; Dr. Nadim Ajami (Baylor) for providing helpful comments on the manuscript; Greg Donaldson (Caltech) for conducting experiments on microbial viability; Dr. Kym Faull (UCLA) for conducting pilot GC/MS experiments; Dr. Alessio Fasano (Massachusetts General) for conducting pilot microbiota sequencing experiments; and Dr. Jerrold Turner (U Chicago) for providing histological analysis of intestinal sections. \n\nThis work was supported by a Caltech Innovation Fellowship (to E.Y.H.), Autism Speaks Weatherstone Fellowship (to E.Y.H.), NIH/NRSA Predoctoral Fellowship (to E.Y.H.), Human Frontiers Science Program Fellowship (to G.S.), DOD Graduate Fellowship (to J.A.C.), NSF Graduate Research Fellowship (to J.A.C.), Autism Speaks Trailblazer Award (to P.H.P. and S.K.M.), Caltech Innovation Initiative (to P.H.P. and S.K.M.), Caltech Grubstake Awards (to P.H.P. and S.K.M), Congressionally Directed Medical Research Award (to\nP.H.P. and S.K.M.), Weston Havens Award (to P.H.P. and S.K.M.), Callie D. McGrath Charitable Foundation awards (to P.H.P.) and NIMH grant MH100556 (to P.H.P. and S.K.M.).",
    revision_no = "36",
    abstract = "Neurodevelopmental disorders, including autism spectrum disorder (ASD), are defined by core behavioral impairments; however, subsets of individuals display a spectrum of gastrointestinal (GI) abnormalities. We demonstrate GI barrier defects and microbiota alterations in the maternal immune activation (MIA) mouse model that is known to display features of ASD. Oral treatment of MIA offspring with the human commensal Bacteroides fragilis corrects gut permeability, alters microbial composition, and ameliorates defects in communicative, stereotypic, anxiety-like and sensorimotor behaviors. MIA offspring display an altered serum metabolomic profile, and B. fragilis modulates levels of several metabolites. Treating naive mice with a metabolite that is increased by MIA and restored by B. fragilis causes certain behavioral abnormalities, suggesting that gut bacterial effects on the host metabolome impact behavior. Taken together, these findings support a gut-microbiome-brain connection in a mouse model of ASD and identify a potential probiotic therapy for GI and particular behavioral symptoms in human neurodevelopmental disorders.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/41318,
    title ="A Unified Strategy to ent-Kauranoid Natural Products: Total Syntheses of (−)-Trichorabdal A and (−)-Longikaurin E",
    author = "Yeoman, John T. S. and Mak, Victor W.",
    journal = "Journal of the American Chemical Society",
    volume = "135",
    number = "32",
    pages = "11764-11767",
    month = "August",
    year = "2013",
    doi = "10.1021/ja406599a   ",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130913-104221740",
    note = "© 2013 American Chemical Society.\n\nReceived: June 28, 2013;\nPublished: July 25, 2013.\n\nWe thank Dr. David VanderVelde for assistance with NMR\nstructure determination, as well as Prof. Brian Stoltz, Dr. Scott\nVirgil, and the Caltech Center for Catalysis and Chemical\nSynthesis for access to analytical equipment. We also thank\nSigma-Aldrich for a kind donation of chemicals. S.E.R. is a\nfellow of the Alfred P. Sloan Foundation and a Camille Dreyfus\nTeacher-Scholar. Fellowship support from Bristol-Myers\nSquibb (J.T.S.Y.) and the National Science Foundation\n(Graduate Research Fellowship, V.W.M., Grant No. DGE-1144469), and financial support from the California Institute of\nTechnology and Amgen, are gratefully acknowledged.",
    revision_no = "14",
    abstract = "The first total syntheses of (−)-trichorabdal A and (−)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (−)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/39742,
    title ="Direct, enantioselective synthesis of pyrroloindolines and indolines from simple indole derivatives",
    author = "Wang, Jane Ni Haoxuan and Reisman, Sarah E.",
    journal = "Tetrahedron",
    volume = "69",
    number = "27-28",
    pages = "5622-5633",
    month = "July",
    year = "2013",
    doi = "10.1016/j.tet.2013.04.003",
    issn = "0040-4020",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130802-142338946",
    note = "© 2013 Elsevier Ltd. Received 18 January 2013. Received in revised form 28 March 2013. Accepted 1 April 2013. Available online 6 April 2013. We thank Dr. David VanderVelde for assistance with NMR structure determination, as well as Prof. Brian Stoltz, Dr. Scott\nVirgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Sigma-Aldrich for a kind donation of chemicals. NMR spectra were obtained on a spectrometer funded by the NIH (RR027690). Fellowship support was provided by Natural Sciences and Engineering Research Council (NSERC) of Canada (J.N., PGS D scholarship). S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the California Institute of Technology, the NIH (NIGMS RGM097582A), and the donors of the ACS Petroleum Research Fund is gratefully acknowledged.",
    revision_no = "14",
    abstract = "The (R)-BINOL·SnCl_4-catalyzed formal (3+2) cycloaddition between 3-substituted indoles and benzyl 2-trifluoroacetamidoacrylate is a direct, enantioselective method to prepare pyrroloindolines from simple starting materials. However, under the originally disclosed conditions, the pyrroloindolines are formed as mixtures of diastereomers, typically in the range of 3:1 to 5:1 favoring the exo-product. The poor diastereoselectivity detracts from the synthetic utility of the reaction. We report here that use of methyl 2-trifluoroacetamidoacrylate in conjunction with (R)-3,3′-dichloro-BINOL·SnCl_4 provides the corresponding pyrroloindolines with improved diastereoselectivity (typically ≥10:1). Guided by mechanistic studies, a one-flask synthesis of enantioenriched indolines by in situ reduction of a persistent iminium ion is also described.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/39270,
    title ="Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones",
    author = "Cherney, Alan H. and Kadunce, Nathaniel T.",
    journal = "Journal of the American Chemical Society",
    volume = "135",
    number = "20",
    pages = "7442-7445",
    month = "May",
    year = "2013",
    doi = "10.1021/ja402922w",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130709-110341676",
    note = "© 2013 American Chemical Society.\n\nReceived: March 22, 2013 Published: May 1, 2013.\n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Sigma-Aldrich for a kind donation of chemicals. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, A.H.C., Grant No. DGE-1144469). S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the California Institute of Technology, Amgen, and Novartis is gratefully acknowledged.\n",
    revision_no = "17",
    abstract = "The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a Ni^(II)/bis(oxazoline) catalyst in the presence of Mn^0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/39168,
    title ="α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation",
    author = "Nani, Roger R. and Reisman, Sarah E.",
    journal = "Journal of the American Chemical Society",
    volume = "135",
    number = "19",
    pages = "7304-7311",
    month = "May",
    year = "2013",
    doi = "10.1021/ja401610p",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130701-134649902",
    note = "© 2013 American Chemical Society.\n\nReceived: February 21, 2013; Published: May 3, 2013.\n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Sigma-Aldrich for a kind donation of chemicals. S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the National Science Foundation (CAREER-1057143), Boehringer-Ingleheim, Amgen, and the California Institute of Technology is gratefully acknowledged. ",
    revision_no = "14",
    abstract = "An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor–acceptor-substituted diazo substrates instead produce mixtures of C–H insertion and dimerization products. α-Diazo-β-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the α-cyano-α-ketocyclopropane products are demonstrated to serve as substrates for S_(N)2, S_(N)2′, and aldehyde cycloaddition reactions.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/38761,
    title ="Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B",
    author = "Kieffer, Madeleine E. and Chuang, Kangway V.",
    journal = "Journal of the American Chemical Society",
    volume = "135",
    number = "15",
    pages = "5557-5560",
    month = "April",
    year = "2013",
    doi = "10.1021/ja4023557",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130603-133349209",
    note = "© 2013 American Chemical Society.\n\nReceived: March 6, 2013; Published: March 29, 2013.\n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Dr. Matthew Winston for samples of L6. We also thank Sigma-Aldrich for a kind donation of chemicals. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowships to M.E.K. and K.V.C., Grant DGE-1144469). S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the California Institute of Technology, Amgen, DuPont, and the NIH(NIGMS RGM097582A) is gratefully acknowledged.",
    revision_no = "17",
    abstract = "A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/38077,
    title ="Pactamycin Made Easy",
    author = "Codelli, Julian A. and Reisman, Sarah E.",
    journal = "Science",
    volume = "340",
    number = "6129",
    pages = "152-153",
    month = "April",
    year = "2013",
    doi = "10.1126/science.1236882",
    issn = "0036-8075",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130423-105804953",
    note = "© 2013 American Association for the Advancement of Science.",
    revision_no = "9",
    abstract = "Natural products—small molecules isolated from plants, fungi, bacteria, and other microorganisms—continue to serve as an important source of chemical tools for the study of biological systems and disease pathology, as well as new drugs. One example is the natural product pactamycin, which has been instrumental in the investigation of ribosome structure and function (1, 2). However, the structural complexity of this small molecule has historically rendered it—and by extension its unnatural analogs—synthetically inaccessible, hindering efforts at the development of pactamycin-derived therapeutics. On page 180 of this issue, Malinowski et al. (3) report a total chemical synthesis of pactamycin that elegantly addresses this challenge and opens a new chapter in the story of this natural product",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/36751,
    title ="Catalytic asymmetric synthesis of highly substituted pyrrolizidines",
    author = "Lim, Andrew D. and Codelli, Julian A.",
    journal = "Chemical Science",
    volume = "4",
    number = "2",
    pages = "650-654",
    month = "November",
    year = "2012",
    doi = "10.1039/c2sc21617e   ",
    issn = "2041-6520",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20130204-094241868",
    note = "© 2013 The Royal Society of Chemistry. \n\nReceived 28th September 2012. Accepted 31st October 2012. First published on the web 13 Nov 2012. \n\nWe thank the late Dr Michael Day and Mr Larry Henling for\nX-ray crystallographic structure determination, Dr David vander\nVelde for assistance with NMR structure determination, as well\nas Prof. Brian Stoltz, Dr Scott Virgil, and the Caltech Center for\nCatalysis and Chemical Synthesis for access to analytical\nequipment. Dr Jacob Cha and Dr. Scott Virgil are acknowledged\nfor assistance with QUINAP preparation. We also thank Sigma-\nAldrich for a kind donation of chemicals. The Bruker KAPPA\nAPEXII X-ray diffractometer was purchased through an award to\nthe California Institute of Technology by the National Science\nFoundation (NSF) CRIF program (CHE-0639094). Fellowship\nsupport was provided by the Department of Defense (DoD)\nthrough the National Defense Science & Engineering Graduate\nFellowship Program (J. A. C.), and by the NSF Graduate Research\nFellowship Program (J. A. C. and A. D. L., Grant no. DGE-\n1144469). S. E. R. is a fellow of the Alfred P. Sloan Foundation\nand a Camille Dreyfus Teacher-Scholar. Financial support from\nthe California Institute of Technology and the NIH (NIGMS\nRGM097582A) is gratefully acknowledged.",
    revision_no = "21",
    abstract = "A catalytic asymmetric double (1,3)-dipolar cycloaddition reaction has been developed. Using a chiral silver catalyst, enantioenriched pyrrolizidines can be prepared in one flask from inexpensive, commercially available starting materials. The pyrrolizidine products contain a variety of substitution patterns and as many as six stereogenic centers.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/35975,
    title ="A copper-catalyzed arylation of tryptamines for the direct synthesis of aryl pyrroloindolines",
    author = "Kieffer, Madeleine E. and Chuang, Kangway V.",
    journal = "Chemical Science",
    volume = "3",
    number = "11",
    pages = "3170-3174",
    month = "November",
    year = "2012",
    doi = "10.1039/c2sc20914d   ",
    issn = "2041-6520",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20121213-102648677",
    note = "© 2012 The Royal Society of Chemistry. \n\nReceived 9th July 2012, Accepted 9th August 2012. First published on the web 17 Aug 2012. \n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech\nCenter for Catalysis and Chemical Synthesis for access to\nanalytical equipment. We also thank Sigma-Aldrich for a kind\ndonation of chemicals. Fellowship support was provided by the\nNational Science Foundation (Graduate Research Fellowship,\nM.E.K, Grant no. DGE-1144469). Financial support from the\nCalifornia Institute of Technology and the NIH (NIGMS\nRGM097582A) is gratefully acknowledged.",
    revision_no = "17",
    abstract = "An operationally simple, copper-catalyzed arylation of N-tosyltryptamines provides direct access to C3-aryl pyrroloindolines. A range of electron-donating and electron-withdrawing substituents is tolerated on both the indole backbone and the aryl electrophile. These reactions occur under ambient temperatures and with equimolar quantities of the coupling partners.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/36048,
    title ="Single molecules put a ring on it",
    author = "Yeoman, John T. S. and Reisman, Sarah E.",
    journal = "Nature",
    volume = "490",
    number = "7419",
    pages = "179-180",
    month = "October",
    year = "2012",
    doi = "10.1038/490179a",
    issn = "0028-0836",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20121219-111243318",
    note = "© 2012 Macmillan Publishers Limited.\nPublished online 10 October 2012.\n",
    revision_no = "13",
    abstract = "A variant of a classical reaction has been used to generate short-lived chemical species called arynes, allowing the one-step synthesis of structurally complex benzene derivatives from simple precursors.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/34842,
    title ="Rapid Construction of the Aza-Propellane Core of Acutumine via a Photochemical [2 + 2] Cycloaddition Reaction",
    author = "Navarro, Raul and Reisman, Sarah E.",
    journal = "Organic Letters",
    volume = "14",
    number = "17",
    pages = "4354-4357",
    month = "September",
    year = "2012",
    doi = "10.1021/ol3017963   ",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20121011-093625947",
    note = "© 2012 American Chemical Society. Received June 29, 2012. Article ASAP August 14, 2012. Published In Issue September 07, 2012. We thank several of our colleagues at the California Institute of Technology: Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structural determination, Dr. David Vander Velde for assistance with NMR structural determination, and Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Fellowship support was provided by the Gates Millennium Scholars Program (R.N.) and the NIH (R.N., F31GM098025). HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE-0639094, CHE-0541745). Financial support from the California Institute of Technology and the NSF (CAREER-1057143) is gratefully acknowledged.",
    revision_no = "30",
    abstract = "Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retro-aldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating an unusual, caged, pentacyclic hemiketal product.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/31544,
    title ="Enantioselective Synthesis of Tryptophan Derivatives by a Tandem Friedel–Crafts Conjugate Addition/Asymmetric Protonation Reaction",
    author = "Kieffer, Madeleine E. and Repka, Lindsay M.",
    journal = "Journal of the American Chemical Society",
    volume = "134",
    number = "11",
    pages = "5131-5137",
    month = "March",
    year = "2012",
    doi = "10.1021/ja209390d",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20120518-141739718",
    note = "© 2012 American Chemical Society.\n\nPublished In Issue March 21, 2012; Article ASAP March 05, 2012; Received: October 05, 2011.\n\nWe thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Dr. David VanderVelde for assistance with NMR structure determination. Fellowship support was provided by the NSF (M. E. K., Graduate Research Fellowship under Grant No. DGE-1144469) and the ACS Division of Organic Chemistry (L.M.R., sponsored by Genentech). Nadine Currie is acknowledged for assistance in the preparation of several indole substrates. Financial support from the California Institute of Technology, the NIH (NIGMS RGM097582A), and the donors of the ACS Petroleum Research Foundation are gratefully acknowledged.",
    revision_no = "35",
    abstract = "The tandem Friedel–Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3′-dibromo-BINOL in the presence of stoichiometric SnCl_4, and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOL·SnCl_4 complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/30141,
    title ="Enantioselective Total Synthesis of (—)-Acetylaranotin, a\nDihydrooxepine Epidithiodiketopiperazine",
    author = "Codelli, Julian A. and Puchlopek, Angela L. A.",
    journal = "Journal of the American Chemical Society",
    volume = "134",
    number = "4",
    pages = "1930-1933",
    month = "February",
    year = "2012",
    doi = "10.1021/ja209354e",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20120417-140414670",
    note = "© 2011 American Chemical Society. Received: October 4, 2011. Publication Date (Web): October 24, 2011. We thank Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structure determination and Dr. David Vander-Velde for assistance with NMR structure determination. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. The Bruker KAPPA APEXII X-ray diffractometer was purchased through an award to the California Institute of Technology by the National Science Foundation (NSF) CRIF program (CHE-0639094). NMR spectra were obtained on a spectrometer funded by the National Institutes of Health (NIH) (RR027690). J.A.C. was supported by the Department of\nDefense (DoD) through the National Defense Science & Engineering Graduate Fellowship Program and by the NSF Graduate Research Fellowship Program (Grant DGE-07032 67). Financial support from the California Institute of Technology and the NIH (NIGMS RGM097582A) is gratefully acknowledged.",
    revision_no = "65",
    abstract = "The first total synthesis of the dihydrooxepine-containing epidithiodiketopiperazine (ETP) (−)-acetylaranotin (1) is reported. The key steps of the synthesis include an enantioselective azomethine ylide (1,3)-dipolar cycloaddition reaction to set the absolute and relative stereochemistry, a rhodium-catalyzed cycloisomerization/chloride elimination sequence to generate the dihydrooxepine moiety, and a stereoretentive diketopiperazine sulfenylation to install the epidisulfide. This synthesis provides access to (−)-1 in 18 steps from inexpensive, commercially available starting materials. We anticipate that the approach described herein will serve as a general strategy for the synthesis of additional members of the dihydrooxepine ETP family.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/28411,
    title ="Buchner and Beyond: Arene Cyclopropanation as Applied to Natural Product Total Synthesis\n",
    author = "Reisman, Sarah E. and Nani, Roger R.",
    journal = "Synlett",
    volume = "2011",
    number = "17",
    pages = "2437-2442",
    month = "October",
    year = "2011",
    doi = "10.1055/s-0031-1289520   ",
    issn = "0936-5214",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20111212-082239823",
    note = "© 2011 Georg Thieme Verlag Stuttgart. Received 25 April 2011. Advanced online publication: 06.10.2011.\nFinancial support from the California Institute of Technology is gratefully acknowledged.",
    revision_no = "18",
    abstract = "Buchner and Curtius first reported the cyclopropanation of arenes in 1885. Since the initial discovery, the Buchner reaction has been the subject of significant research by both physical and synthetic organic chemists. Described herein is a brief overview of the Buchner reaction and related arene cyclopropanation processes, with an emphasis on their application to natural product total synthesis.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/27507,
    title ="A Concise Total Synthesis of (--)-Maoecrystal Z",
    author = "Cha, Jacob Y. and Yeoman, John T. S.",
    journal = "Journal of the American Chemical Society",
    volume = "133",
    number = "38",
    pages = "14964-14967",
    month = "September",
    year = "2011",
    doi = "10.1021/ja2073356 ",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20111031-072905834",
    note = "© 2011 American Chemical Society. Received: August 4, 2011. Publication Date (Web): August 30, 2011. We thank Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structure determination and Dr. David Vander-Velde for assistance with NMR structure determination. We thank Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Dr. Scott Virgil for insightful discussions. The Bruker KAPPA APEXII X-ray diffractometer was purchased through an award to the California Institute of Technology by the NSF CRIF program (CHE-0639094). Financial support from the California Institute of Technology is gratefully acknowledged. ",
    revision_no = "36",
    abstract = "The first total synthesis of (--)-maoecrystal Z\nis described. The key steps of the synthesis include a\ndiastereoselective Ti^(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm^(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (--)-maoecrystal Z in only 12 steps from (--)-γ-cyclogeraniol.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/26589,
    title ="Short, Enantioselective Total Syntheses of (—)-8-Demethoxyrunanine and (—)-Cepharatines A, C, and D",
    author = "Chuang, Kangway V. and Navarro, Raul",
    journal = "Angewandte Chemie International Edition",
    volume = "50",
    number = "40",
    pages = "9447-9451",
    month = "September",
    year = "2011",
    doi = "10.1002/anie.201104487",
    issn = "1433-7851",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20111005-093543509",
    note = "© 2011 Wiley-VCH Verlag GmbH & Co. \n\nIssue published online: 21 Sep 2011. Article first published online: 30 Aug 2011. Manuscript Received: 29 Jun 2011. \n\nWe thank Dr. Michael Day and Mr. Larry Henling for X-ray crystallographic structural determination, as well as Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Fellowship support was provided by the Gates Millennium Scholars Program (R.N.), the NIH (R.N., 1F31GM098025A) and the Amgen Scholars Program (K.V.C.). HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE-0639094, CHE-0541745). Financial support from the California Institute of Technology and the NSF (CAREER-1057143) is gratefully acknowledged.",
    revision_no = "22",
    abstract = "All together! A unified synthetic strategy has resulted in the first enantioselective total syntheses of the natural products 8-demethoxyrunanine and cepharatines\u2005A, C, and D.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/23894,
    title ="Medicinal chemistry: New lead for pain treatment\n",
    author = "Reisman, Sarah E.",
    journal = "Nature",
    volume = "473",
    number = "7348",
    pages = "458-459",
    month = "May",
    year = "2011",
    doi = "10.1038/473458a",
    issn = "0028-0836",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20110603-093858950",
    note = "© 2011 Macmillan Publishers Limited. \n\nPublished online 25 May 2011.",
    revision_no = "13",
    abstract = "The synthesis of conolidine, a scarce, naturally occurring compound, has enabled the first studies of its pharmacological properties to be carried out. Excitingly, conolidine is a painkiller that seems to have an unusual mechanism of action.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/23916,
    title ="Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone",
    author = "Chuang, Kangway V. and Navarro, Raul",
    journal = "Chemical Science",
    volume = "2",
    number = "6",
    pages = "1086-1089",
    month = "May",
    year = "2011",
    doi = "10.1039/C1SC00095K",
    issn = "2041-6520",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20110606-112443200",
    note = "© 2011 The Royal Society of Chemistry. \n\nReceived 16th February 2011, Accepted 25th February 2011. First published on the web 25 Mar 2011. \n\nWe thank Drs. Michael Day and Larry Henling for X-ray crystallographic structural determination, as well as Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank\nthe Gates Millennium Scholars Program (R.N.) and the Amgen\nScholars Program (K.V.C.) for fellowship support. Andrew Lim\nis acknowledged for assistance in the preparation of compound 10. HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE-0639094, CHE-0541745). Financial support from the California Institute of Technology is gratefully acknowledged.  ",
    revision_no = "27",
    abstract = "The preparation and synthetic applications of benzoquinone monoketal-derived N-tert-butanesulfinyl imines is described. These synthetically versatile intermediates undergo highly diastereoselective 1,2-addition reactions with organometallic reagents to provide 4-aminocyclohexadienones in good yields. The utility of this methodology is demonstrated in a six-step enantioselective synthesis of (–)-3-demethoxyerythratidinone.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/23020,
    title ="Enantioselective Total Synthesis of (+)-Salvileucalin B",
    author = "Levin, Sergiy and Nani, Roger R.",
    journal = "Journal of the American Chemical Society",
    volume = "133",
    number = "4",
    pages = "774-776",
    month = "February",
    year = "2011",
    doi = "10.1021/ja110192b ",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20110321-160052573",
    note = "© 2010 American Chemical Society.\n\nReceived: November 12, 2010.\nArticle ASAP\nDecember 21, 2010.\nPublished In Issue \nFebruary 02, 2011.\n\nWe thank Drs. Michael Day and Larry Henling for X-ray\ncrystallographic structural determination and Dr. Scott Virgil for\ninsightful discussions. We thank Prof. Brian Stoltz and the\nCaltech Center for Catalysis and Chemical Synthesis for access\nto analytical equipment. HRMS and X-ray crystallographic data\nwere obtained on instruments purchased through awards to the\nCalifornia Institute of Technology by the NSF CRIF program\n(CHE-0639094, CHE-0541745). Ms. Kendra Joseph is acknowledged\nfor assistance in the preparation of alkyne 9. Financial\nsupport from the California Institute of Technology is gratefully\nacknowledged.",
    revision_no = "25",
    abstract = "An enantioselective total synthesis of the diterpenoid natural product   (+)-salvileucalin B is reported. Key findings include a\n   copper-catalyzed arene cyclopropanation reaction to provide the unusual\n   norcaradiene core and a reversible retro-Claisen rearrangement of a\n   highly functionalized norcaradiene intermediate.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/20719,
    title ="Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction\n",
    author = "Repka, Lindsay M. and Ni, Jane",
    journal = "Journal of the American Chemical Society",
    volume = "132",
    number = "41",
    pages = "14418-14420",
    month = "October",
    year = "2010",
    doi = "10.1021/ja107328g ",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20101108-140057935",
    note = "© 2010 American Chemical Society.\nReceived August 23, 2010. Publication Date (Web): September 27, 2010.  Published In Issue October 20, 2010\n\nWe thank Dr. Scott Virgil for insightful\ndiscussions; Drs. Michael Day and Larry Henling for X-ray\ncrystallographic structural determination; and Prof. Brian Stoltz and\nthe Caltech Center for Catalysis and Chemical Synthesis for access\nto analytical equipment. HRMS and X-ray crystallographic data\nwere obtained on instruments purchased through awards to the\nCalifornia Institute of Technology by the NSF CRIF program (CHE-\n0639094, CHE-0541745). NMR spectra were obtained on a\nspectrometer funded by the NIH (RR027690). Financial support\nfrom the California Institute of Technology and the Baxter\nFoundation is gratefully acknowledged.\n\nSupporting Information: Experimental details, characterization data, and NMR spectral charts. This material is available free of charge via the Internet at http://pubs.acs.org.",
    revision_no = "27",
    abstract = "(R)-BINOL•SnCl_4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/52995,
    title ="Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition",
    author = "Freeman, David B. and Holubec, Alexandra A.",
    journal = "Tetrahedron",
    volume = "66",
    number = "33",
    pages = "6647-6655",
    month = "August",
    year = "2010",
    doi = "10.1016/j.tet.2010.04.131",
    issn = "0040-4020",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20141217-164835707",
    note = "Copyright © 2010 Elsevier. \n\nReceived 1 March 2010; Received in revised form 21 April 2010; Accepted 29 April 2010; Available online 6 May 2010. \n\n2009 Tetrahedron Prize for Creativity in Organic Chemistry. \n\nDedicated to Professor Steven Ley, a friend and inspirational leader in organic chemistry. \n\nFunding from the NIH (1 RO1 CA 93591), Astellas (formerly Yamanouchi), Daiichi, and Fujisawa are gratefully acknowledged. MI thanks the University of Tokyo School of Agricultural Sciences. JLW thanks Amgen, Merck, Bristol-Myers Squibb, GlaxoSmithKline and Pfizer for research support. RNT would like to acknowledge the Jack and June Richardson Honors Scholarship Fund and the CSU CNS Undergraduate Scholarship Fund for financial support. Dr. Chris Incarvito, Dr. Chris Rithner, Don Heyse and Don Dick are acknowledged for their assistance with X-ray crystallography and instrumentation.",
    revision_no = "15",
    abstract = "Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O–H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/17649,
    title ="Rapid Assembly of the Salvileucalin B Norcaradiene Core",
    author = "Levin, Sergiy and Nani, Roger R.",
    journal = "Organic Letters",
    volume = "12",
    number = "4",
    pages = "780-783",
    month = "February",
    year = "2010",
    doi = "10.1021/ol902848k",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20100303-133732724",
    note = "© 2010 American Chemical Society.\nReceived December 10, 2009.\nPublication Date (Web): January 20, 2010.\nWe thank Dr. Scott Virgil and Dr.\nJennifer Roizen of the California Institute of Technology for\ninsightful discussions, as well as Prof. Brian Stoltz and the\nCaltech Center for Catalysis and Chemical Synthesis for\naccess to analytical equipment. Financial support from the\nCalifornia Institute of Technology is gratefully acknowledged.\n",
    revision_no = "23",
    abstract = "Preparation of the polycyclic core of the cytotoxic natural product salvileucalin B is described. The key feature of this synthetic strategy is a copper-catalyzed intramolecular arene cyclopropanation to provide the central norcaradiene. These studies lay the foundation for continued investigations toward an enantioselective total synthesis of 1.\n",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75607,
    title ="Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions",
    author = "Reisman, Sarah E. and Doyle, Abigail G.",
    journal = "Journal of the American Chemical Society",
    volume = "130",
    number = "23",
    pages = "7198-7199",
    month = "June",
    year = "2008",
    doi = "10.1021/ja801514m",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170331-155430409",
    note = "© 2008 American Chemical Society. \n\nReceived February 28, 2008; Publication Date (Web): May 14, 2008. \n\nThis work was supported by the NIGMS (GM-43214), by predoctoral fellowship support to A.G.D. from the NSF, and postdoctoral fellowship to S.E.R. from the NIH. We thank Dr. Kevin Campos (Merck Process) for helpful discussions and generous donations of N-Boc-2-arylpyrrolidine derivatives.",
    revision_no = "16",
    abstract = "Asymmetric, catalytic reactions of oxocarbenium ions are reported. Simple, chiral urea and thiourea derivatives are shown to catalyze the enantioselective substitution of silyl ketene acetals onto 1-chloroisochromans. A mechanism involving anion binding by the chiral catalyst to generate a reactive oxocarbenium ion is invoked. Catalysts bearing tertiary benzylic amide groups afforded highest enantioselectivities, with the optimal structure being derived from enantioenriched 2-arylpyrrolidine derivatives.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75606,
    title ="Evolution of a Synthetic Strategy: Total Synthesis of (±)-Welwitindolinone A Isonitrile",
    author = "Reisman, Sarah E. and Ready, Joseph M.",
    journal = "Journal of the American Chemical Society",
    volume = "130",
    number = "6",
    pages = "2087-2100",
    month = "February",
    year = "2008",
    doi = "10.1021/ja076663z",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170331-150127498",
    note = "© 2008 American Chemical Society. \n\nReceived September 19, 2007; Publication Date (Web): January 17, 2008. \n\nFinancial support was provided by Bristol-Myers Squibb, Yamanouchi, Merck, Amgen, Pfizer, and the NIH (Grant No. 1 RO1 CA/GM 93591-01A). S.E.R. thanks Bristol-Myers Squibb for a graduate student fellowship. J.M.R. was the recipient of a NIH postdoctoral fellowship. In addition, we acknowledge and thank C.D. Incarvito for X-ray crystallographic analysis.",
    revision_no = "20",
    abstract = "An efficient and highly stereoselective total synthesis of the natural product (±)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a SmI_2−LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75605,
    title ="Total Synthesis of (±)-Welwitindolinone A Isonitrile",
    author = "Reisman, Sarah E. and Ready, Joseph M.",
    journal = "Journal of the American Chemical Society",
    volume = "128",
    number = "5",
    pages = "1448-1449",
    month = "February",
    year = "2006",
    doi = "10.1021/ja057640s",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170331-145008719",
    note = "© 2006 American Chemical Society. \n\nReceived November 9, 2005; Publication Date (Web): January 11, 2006. \n\nFinancial support was provided by Bristol-Myers Squibb, Yamanouchi, Merck, Amgen, Pfizer, and the NIH (Grant No. 1 R01 CA/GM 93591-01A). S.E.R. thanks Bristol-Myers Squibb for a graduate student fellowship. J.M.R. was the recipient of a NIH postdoctoral fellowship. In addition, we acknowledge and thank C.D. Incarvito for X-ray crystallographic analysis.",
    revision_no = "18",
    abstract = "A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol. ",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75662,
    title ="A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A Isonitrile",
    author = "Ready, Joseph M. and Reisman, Sarah E.",
    journal = "Angewandte Chemie International Edition",
    volume = "43",
    number = "10",
    pages = "1270-1272",
    month = "February",
    year = "2004",
    doi = "10.1002/anie.200353282",
    issn = "1433-7851",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170404-071621138",
    note = "© 2004 WILEY-VCH Verlag GmbH & Co. \n\nIssue online: 25 Feb 2004. Version of Record online: 11 Feb 2004. Manuscript Received: 10 Nov 2003. \n\nWe gratefully acknowledge financial support from Yamanouchi, Merck, Pfizer, and Amgen. J.M.R. is the recipient of an NIH postdoctoral fellowship. K.R. thanks Sankyo Co., LTD.; M.H. thanks Daiso Co., LTD., M.M.W. thanks Bristol Myers Squibb for a graduate fellowship.",
    revision_no = "12",
    abstract = "The complete carbon skeleton of welwitindolinone A isonitrile has been prepared by using a [2+2] cycloaddition to establish the bicyclo[4.2.0]octane core and a SmI2-mediated intramolecular reductive cyclization between an enone and an aryl isocyanate to stereoselectively install the spiro-oxindole (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene).",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/75656,
    title ="Facile Entry to the Tetracyclic 5-7-6-3 Tigliane Ring System",
    author = "Ovaska, Timo V. and Reisman, Sarah E.",
    journal = "Organic Letters",
    volume = "3",
    number = "1",
    pages = "115-117",
    month = "January",
    year = "2001",
    doi = "10.1021/ol006823a",
    issn = "1523-7060",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20170403-155648365",
    note = "© 2001 American Chemical Society. \n\nReceived November 3, 2000. Publication Date (Web): December 15, 2000. \n\nThis work was supported by grants from the donors of the Petroleum Research Fund, administered by the American Chemical Society, the Research Corporation (Cottrell College Science Award), and the National Institutes of Health (GM60972-01). S.E.R. and M.A.F. acknowledge Pfizer, Inc., for Summer Fellowships (Pfizer Summer Undergraduate Fellowship and PREPARE programs). We are also grateful to Dr. Walt Massefski of Pfizer Central Research, Groton, CT, for performing a complete NMR analysis of compound 16. ",
    revision_no = "14",
    abstract = "A tandem anionic 5-exo-dig cyclization/Claisen rearrangement sequence was used to effect a facile, “one-pot” conversion of an appropriately substituted 4-alkyn-1-ol to the tetracyclic carbon core structure of phorbol. The synthesis was conducted using readily available nonracemic starting materials to provide the target structure as a single enantiomer in high chemical yield.",
}