@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/107875,
    title ="Total Synthesis of Ritterazine B",
    author = "Nakayama, Yasuaki and Maser, Michael R.",
    journal = "Journal of the American Chemical Society",
    volume = "143",
    number = "11",
    pages = "4187-4192",
    month = "March",
    year = "2021",
    doi = "10.1021/jacs.1c01372",
    issn = "0002-7863",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20210202-123615131",
    note = "© 2021 American Chemical Society. \n\nReceived: February 4, 2021;\nPublished: March 9, 2021.\n\nDr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. We thank Arthur Han for early studies. Fellowship support was provided by the NSF (M.R.M., Grant No. DGE-1144469), the Japan Society for the Promotion of Science (Y.N.), and Ishihara Sangyo Kaisha, Ltd. (T.O.). S.E.R. is a Heritage Medical Research Institute Investigator and acknowledges financial support from the American Cancer Society. \n\nThe authors declare no competing financial interest.",
    revision_no = "28",
    abstract = "The first total synthesis of the cytotoxic alkaloid ritterazine B is reported. The synthesis features a unified approach to both steroid subunits, employing a titanium-mediated propargylation reaction to achieve divergence from a common precursor. Other key steps include gold-catalyzed cycloisomerizations that install both spiroketals and late stage C–H oxidation to incorporate the C7′ alcohol.",
}
@article {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/108172,
    title ="Synthesis of Complex Diterpenes: Strategies Guided by Oxidation Pattern Analysis",
    author = "Dibrell, Sara E. and Tao, Yujia",
    journal = "Accounts of Chemical Research",
    volume = "54",
    number = "6",
    pages = "1360-1373",
    month = "March",
    year = "2021",
    doi = "10.1021/acs.accounts.0c00858",
    issn = "0001-4842",
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20210224-121416493",
    note = "© 2021 American Chemical Society. \n\nReceived: December 17, 2020; Publication Date: February 23, 2021. \n\nPublished as part of the Accounts of Chemical Research special issue “Total Synthesis of Natural Products”.\n\nWe would like to gratefully acknowledge the past and present members of the Reisman laboratory who have contributed to the science that is captured in this Account. Fellowship support was provided by the NSF (S.E.D., Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191) is acknowledged. \n\nThe authors declare no competing financial interest.",
    revision_no = "12",
    abstract = "Conspectus: With complex molecular architectures, intriguing oxidation patterns, and wide-ranging biological activities, diterpene natural products have greatly impacted research in organic chemistry and drug discovery. Our laboratory has completed total syntheses of several highly oxidized diterpenes, including the ent-kauranoids maoecrystal Z, trichorabdal A, and longikaurin E; the antibiotic pleuromutilin; and the insecticides ryanodol, ryanodine, and perseanol. In this Account, we show how analysis of oxidation patterns and inherent functional group relationships can inform key C–C bond disconnections that greatly simplify the complexity of polycyclic structures and streamline their total syntheses. In articulating these concepts, we draw heavily from the approaches to synthetic strategy that were codified by Evans, Corey, Seebach, and others, based on the formalism that heteroatoms impose an alternating acceptor and donor reactivity pattern upon a carbon skeleton. We find these ideas particularly useful when considering oxidized diterpenes as synthetic targets.\nIn the first part of the Account, we describe the use of reductive cyclizations as strategic tactics for building polycyclic systems with γ-hydroxyketone motifs. We have leveraged Sm-ketyl radical cyclizations as “reactivity umpolungs” to generate γ-hydroxyketones in our total syntheses of the Isodonent-kauranoid diterpenes (−)-maoecrystal Z, (−)-longikaurin E, and (−)-trichorabdal A. Following this work, we identified the same γ-hydroxyketone pattern in the diterpene antibiotic (+)-pleuromutilin, which again inspired the use of a SmI₂-mediated reductive cyclization, this time to construct a bridging eight-membered ring. This collection of four total syntheses highlights how reductive cyclizations are particularly effective umpolung tactics when used to simultaneously form rings and introduce 1,4-dioxygenation patterns. \n\nIn the second part of the Account, we detail the syntheses of the complex and highly oxidized ryanodane and isoryanodane diterpenes and present the oxidation pattern analysis that guided our synthetic designs. We first discuss our 15-step total synthesis of (+)-ryanodol, which incorporated five of the eight oxygen atoms in just two transformations: a dihydroxylation of (S)-pulegone and a SeO₂-mediated trioxidation of the A-ring cyclopentenone. This latter transformation gave rise to an independent investigation of SeO₂-mediated peroxidations of simple bicyclic cyclopent-2-en-1-ones. The syntheses of (+)-ryanodine and (+)-20-deoxyspiganthine are also presented, which required modified end-game strategies to selectively incorporate the key pyrrole-2-carboxylate ester. Finally, we describe our fragment coupling approach to prepare the isoryanodane diterpene (+)-perseanol. Using a similar oxidation pattern analysis to that developed in the synthesis of ryanodol, we again identified a two-stage strategy to install the five hydroxyl groups. This strategy was enabled by a Pd-mediated carbopalladation/carbonylation cascade and leveraged unexpected, emergent reactivity to sequence a series of late-stage oxidations. \n\nWhile each of the diterpene natural products discussed in this Account present unique synthetic questions, we hope that through their collective discussion, we provide a conceptual framework that condenses and summarizes the chemical knowledge we have learned and inspires future discourse and innovations in strategy design and methodology development.\n",
}
@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/107462,
    title ="Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides",
    author = "DeLano, Travis J. and Dibrell, Sara E.",
    
    
    
    
    month = "January",
    year = "2021",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20210113-152642442",
    note = "License: CC BY-NC-ND 4.0. \n\nHistory: 03.01.2021 - Submission date; 04.01.2021 - First online date, Posted date. \n\nDr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. We thank Yoshihiro Ogura for early studies and Raymond Turro for the preparation of L1. M. S. S. thanks the NIH (R35 GM136271) for support. Fellowship support was provided by the NSF (T. J. D., S. E. D., C. R. L., K. E. P., Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator, and acknowledges financial support from the NIH (R35 GM118191).\n\nDeclaration of Conflict of Interest: No conflict of interest.",
    revision_no = "15",
    abstract = "An asymmetric reductive cross-coupling of alpha-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording alpha-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the alpha-chloroester substrate and ligand on enantioselectivity.",
}
@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/106598,
    title ="Graph Neural Networks for the Prediction of Substrate-Specific Organic Reaction Conditions",
    author = "Ryou, Serim and Maser, Michael R.",
    journal = "arXiv",
    
    
    
    month = "July",
    year = "2020",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20201110-154207213",
    note = "© 2020 by the author(s). \n\nTo appear in the ICML 2020 Workshop on Graph Representation\nLearning and Beyond (GRLB). \n\nWe thank the reviewers for their insightful comments and Prof Pietro Perona for mentorship guidance and helpful discussions on this work. 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 Investigator. Financial support from the Research Corporation Cottrell Scholars Program is acknowledged.",
    revision_no = "8",
    abstract = "We present a systematic investigation using graph neural networks (GNNs) to model organic chemical reactions. To do so, we prepared a dataset collection of four ubiquitous reactions from the organic chemistry literature. We evaluate seven different GNN architectures for classification tasks pertaining to the identification of experimental reagents and conditions. We find that models are able to identify specific graph features that affect reaction conditions and lead to accurate predictions. The results herein show great promise in advancing molecular machine learning.",
}
@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.",
}
@conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/101393,
    title ="Necessity is the mother of invention: Natural products and the chemistry they inspire",
    author = "Reisman, Sarah E.",
    
    
    
    pages = "ORGN-0102",
    month = "March",
    year = "2020",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200219-133123539",
    note = "© 2020 American Chemical Society.",
    revision_no = "9",
    abstract = "The chem. synthesis of natural products provides an exciting platform from which to conduct fundamental research in chem. and biol. Our group is currently pursuing the synthesis of a no. of structurally complex natural products, including the diterpenoids perseanol and talatisamine. The densely-packed arrays of heteroatoms and stereogenic centers that constitute these polycyclic targets challenge the limits of current technol. and inspire the development of new synthetic strategies and tactics. This seminar will describe the latest progress in our methodol. and target-directed synthesis endeavors.",
}
@conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/101378,
    title ="Total synthesis of natural product antibiotics",
    author = "Reisman, Sarah E.",
    
    
    
    pages = "ORGN-0427",
    month = "March",
    year = "2020",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20200219-113059736",
    note = "© 2020 American Chemical Society.",
    revision_no = "9",
    abstract = "Since the discovery of the antibiotic penicillin, natural products-small mols. isolated from plants, bacteria, and fungi-have played an essential role in the development of new anti-infectives. Synthetic org. chemists can use Nature's mols. as a starting point, and perform precise mol. edits to make new mols. with improved the properties or efficacy. Although semisynthesis has given rise to the vast majority of natural product-derived antibiotics, total synthesis can provide opportunities to prep. new derivs. not accessible through semi-synthesis. This seminar will describe recent efforts in our lab. focused on the synthesis of natural product antibiotics.",
}
@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.",
}
@conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/97757,
    title ="Building bridges: Strategies for the synthesis of polycyclic natural products",
    author = "Reisman, Sarah E.",
    
    
    
    pages = "ORGN-0104",
    month = "August",
    year = "2019",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190812-092833141",
    note = "© 2019 American Chemical Society.",
    revision_no = "10",
    abstract = "The chem. synthesis of natural products provides an exciting platform from which to conduct fundamental research in chem. and biol. An area of ongoing research in our lab. is the synthesis of the ryanoid and isoryanoid natural products. The densely-packed arrays of hydroxyl groups that constitute these polycyclic targets challenge the limits of current technol. and inspire the development of new synthetic strategies and tactics. This seminar will describe our latest progress in our synthetic efforts towards the isoryanoids.",
}
@conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/97777,
    title ="Development of Ni-catalyzed enantioselective reductive cross-coupling reactions",
    author = "Reisman, Sarah E.",
    
    
    
    pages = "ORGN-0053",
    month = "August",
    year = "2019",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190812-131105027",
    note = "© 2019 American Chemical Society.",
    revision_no = "9",
    abstract = "Nickel catalyzed cross-coupling reactions have emerged as powerful methods to form C(sp^3)-C(sp^2) and C(sp^3)-C(sp^3) bonds. Ni-catalyzed reductive cross-coupling reactions have proven particularly useful for the cross-coupling of secondary alkyl electrophiles, often providing chiral products as racemic mixts. Recognizing that the ability to render these transformations enantioselective would enhance their impact, our lab. has developed enantioselective Ni-catalyzed reductive cross-coupling reactions of an array of org. electrophiles. This seminar will discuss our recent progress in this area.",
}
@conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/97764,
    title ="Necessity is the mother of invention: Natural products and the chemistry they inspire",
    author = "Reisman, Sarah E.",
    
    
    
    pages = "ORGN-0374",
    month = "August",
    year = "2019",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190812-100104064",
    note = "© 2019 American Chemical Society.",
    revision_no = "9",
    abstract = "The chem. synthesis of natural products serves to drive innovation in, and deepen our fundamental understanding of, org. and organometallic chem. In order to enable the prepn. of bioactive mols. with increased complexity, it is imperative to develop both the synthetic tools and the synthetic logic for assembling mols. with complex, stereochem.-rich polycyclic frameworks. One class of targets that challenges existing strategies and methods for chem. synthesis are the diterpenoid alkaloids. This seminar will describe our latest progress in target-directed synthesis endeavors towards this complex family of natural products.",
}
@conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/94098,
    title ="Progress toward the total synthesis of falcatin A",
    author = "Mendoza, Skyler Dakota and Reisman, Sarah E.",
    
    
    
    pages = "PROF-0020",
    month = "April",
    year = "2019",
    
    
    
    url = "https://resolver.caltech.edu/CaltechAUTHORS:20190325-091013157",
    note = "© 2019 American Chemical Society.",
    revision_no = "10",
    abstract = "GIRK channels (G protein mediated inwardly-rectifying potassium ion channels) have been shown to regulate the elec. activity of several cell types including neurons, cardiac atrial myocytes, and b-pancreatic cells. As such, the malfunction of GIRK channels has also been implicated in disorders such as neuropathic pain, drug addiction, and cardiac arrhythmias. Falcatin A is a myrsinane diterpenoid that possesses inhibitory activity against GIRK channels with an IC50 value of 2.5 ± 0.2 uM. We hypothesize that the 5/7/6 carbocyclic framework of the natural product could be constructed\nin a single step through a combination of hydrogen bonding, hydrogen atom transfer, and photoredox catalysis to bring together two complex fragments in a convergent coupling strategy, allowing for the rapid and efficient synthesis of falcatin A and analogs. The synthesis and studies of falcatin A and its analogs could potentially provide some insight into the modulation of GIRK channels. Herein, we describe our synthetic progress toward the total synthesis of falcatin A.",
}