@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.", } @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.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/90577, title ="Synthetic studies toward ryanodol, ryanodine, and related insecticidal natural products", author = "Reisman, Sarah", pages = "AGRO-135", month = "August", year = "2018", url = "https://resolver.caltech.edu/CaltechAUTHORS:20181101-132923115", note = "© 2018 American Chemical Society.", revision_no = "9", abstract = "(+)-Ryanodine was first identified in 1948 by Folkers and coworkers as part of an effort to identify the insecticidal\nconstituents of Ryania speciosa Vahl, a shrub native to Central and South America. In fact, the crude ext. from the shrub\nwas marketed as Ryanex, a non-specific insecticide. However, this product was later removed from the market and\nefforts to make improved ryanodine-derived insecticides have been thwarted by challenging synthetic chem. In this\nseminar, we will describe a synthetic strategy that provides access to (+)-ryanodine and the related natural product (+)-\n20-deoxyspiganthine in 18 and 19 steps, resp. A key feature of this strategy is the reductive cyclization of an epoxide\nintermediate that possesses the crit. pyrrole-2-carboxylate ester. We will also describe recent efforts to prep. the\nantifeedant isoryanoid natural product perseanol.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/85811, title ="Necessity is the mother of invention: Natural products and the chemistry they inspire", author = "Reisman, Sarah", pages = "ORGN-520", month = "March", year = "2018", url = "https://resolver.caltech.edu/CaltechAUTHORS:20180413-084731744", note = "© 2018 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. Our group is currently pursuing the synthesis of a no. of structurally complex natural products, including the\nditerpenoids ryanodine and talatisamine, and the antibiotic pleuromutilin. The densely-packed arrays of heteroatoms and\nstereogenic 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/81397, title ="Building bridges: Strategies and tactics for the synthesis of polycyclic natural products", author = "Reisman, Sarah", pages = "ORGN-195", month = "August", year = "2017", url = "https://resolver.caltech.edu/CaltechAUTHORS:20170913-083334553", note = "© 2017 American Chemical Society.", revision_no = "9", abstract = "The chem. synthesis of natural products provides an exciting platform from which to conduct fundamental\nresearch in chem. and biol. An area of ongoing research in our lab. is the synthesis of polyhydroxylated\nditerpenoids, such as ryanodol and ryanodine, as well as several members of the diterpenoid alkaloids. The\ndensely-packed arrays of heteroatoms and stereogenic centers that constitute these polycyclic targets\nchallenge the limits of current technol. and inspire the development of new synthetic strategies and tactics.\nThis seminar will describe our latest progress in our target directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/81322, title ="Enantioselective Ni-catalyzed cross-electrophile coupling", author = "Reisman, Sarah E.", pages = "ORGN-247", month = "August", year = "2017", url = "https://resolver.caltech.edu/CaltechAUTHORS:20170911-152059005", note = "© 2017 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\ncross-coupling of secondary alkyl electrophiles, often providing chiral products as racemic mixts. Recognizing\nthat the ability to render these transformations enantioselective would enhance their utility, our lab. has\nrecently developed enantioselective Ni-catalyzed reductive cross-coupling reactions of an array of org.\nelectrophiles. This seminar will discuss our recent progress in this area.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/77116, title ="Development of a unified strategy for the syntheis of enmein-type ent-kauranoids", author = "Beck, Jordan C. and Reisman, Sarah E.", pages = "PROF-9", month = "April", year = "2017", url = "https://resolver.caltech.edu/CaltechAUTHORS:20170502-080053912", note = "© 2017 American Chemical Society.", revision_no = "11", abstract = "Development of a unified strategy for the total synthesis of the enmein-type ent-Kauranoids is disclosed. A total synthesis campaign of this class of natural products is of particular interest due to the potent anti-proliferative activity of these natural products across a wide range of cancer cell lines. The synthetic strategy described relies upon formation of the central lactone unit through a challenging reductive crosselectrophile coupling reaction. This route is highly convergent, as it assembles the reductive coupling substrate through an esterification reaction of a stereochem.-rich epoxy alc. with a structurally complex [3.2.1|-bicyclooctane. The epoxy alc. can be assembled through a diastereoselective oxidn. sequence while the [3.2.1|-bicyclooctane can be prepd. through a gold-catalyzed Conia-ene reaction. The modularity of this synthesis can potentially provide access to a wide range of natural products with varying backbone functionalization. Current efforts directed toward the development of key reactions in this sequence and their application to the synthesis of these products will be presented.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/77164, title ="Necessity is the mother of invention: Natural products and the chemistry they inspire", author = "Reisman, Sarah E.", pages = "ORGN-335", month = "April", year = "2017", url = "https://resolver.caltech.edu/CaltechAUTHORS:20170503-143336033", note = "© 2017 American Chemical Society.", revision_no = "8", abstract = "The chem. synthesis of natural products provides an exciting platform from which to conduct fundamental research in chem. and biol. We are currently focused on devising concise approaches to complex polycyclic natural products such as ryanodol, acutumine, and members of the diterpenoid alkaloids. 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 our latest progress in both our methodol. and target-directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/77153, title ="Nickel-catalyzed asymmetric reductive cross-couplings with vinyl bromide electrophiles", author = "Hofstra, Julie and Suzuki, Naoyuki", pages = "ORGN-222", month = "April", year = "2017", url = "https://resolver.caltech.edu/CaltechAUTHORS:20170503-104847932", note = "© 2017 American Chemical Society.", revision_no = "11", abstract = "Nickel-catalyzed reductive cross-coupling reactions allow for the use of bench-stable electrophiles as both\ncross-coupling partners. In an effort to broaden the range of viable substrates in asym. transformations, two \nnew cross-coupling reactions using vinyl bromide electrophiles were developed. The cross-coupling of \nvinyl bromides with chlorobenzyl silanes in the presence of a chiral nickel bis(oxazoline) catalyst and \nstoichiometric manganese reductant delivers chiral allyl silane products with excellent enantioselectivity. These \nproducts are known to participate in diastereoselective allylation reactions that form addnl. stereocenters, \nbuilding mol. complexity. Application of the same catalyst-ligand system to the cross-coupling of vinyl\nbromides with N-hydroxyphthalimide esters gives rise to chiral allylic stereocenters in the presence of\ntetrakis(dimethylamino)ethylene as a terminal org. reductant.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/70292, title ="Enantioselective Ni-catalyzed reductive cross-coupling reactions", author = "Reisman, Sarah", pages = "ORGN-381", month = "August", year = "2016", url = "https://resolver.caltech.edu/CaltechAUTHORS:20160913-083628711", note = "© 2016 American Chemical Society.", revision_no = "10", abstract = "Nickel-catalyzed reductive cross-coupling reactions have emerged as direct\nbond formation. These reactions typically tolerate an array of functional groups,\nand employ inexpensive, earth abundant metals as stoichiometric reductants. May\nrequire the use of pre-generated organometallic reagents. In order to realize the\ncatalyzed reductive cross-coupling reactions, it is crit. to develop enantioselective\ntransformations. This seminar will describe our recent successes in the develop\nenantioselective cross-coupling reactions.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/70310, title ="Necessity is the mother of invention: Natural products and the chemistry they inspire", author = "Reisman, Sarah", pages = "ORGN-57", month = "August", year = "2016", url = "https://resolver.caltech.edu/CaltechAUTHORS:20160913-122803637", note = "© 2016 American Chemical Society.", revision_no = "11", abstract = "The chem. synthesis of natural products provides an exciting platform from which to conduct fundamental research in\nchem. and biol. We are currently focused on devising concise approaches to complex polycyclic natural products such\nas ryanodol, acutumine, and members of the diterpenoid alkaloids. The densely packed arrays of heteroatoms and\nstereogenic centers that constitute these polycyclic targets challenge the limits of current technol. and inspire the\ndevelopment of new synthetic strategies and tactics. This seminar will describe our latest progress in both our methodol.\nand target-directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/60282, title ="Progress toward the total synthesis of psiguadial B", author = "Chapman, Lauren M. and Reisman, Sarah E.", pages = "ORGN-195", month = "August", year = "2015", url = "https://resolver.caltech.edu/CaltechAUTHORS:20150916-130810447", note = "© 2015 American Chemical Society.", revision_no = "10", abstract = "Progress toward the total synthesis of psiguadial B, a diformyl phloroglucinol meroterpenoid natural\nproduct, is disclosed. The synthetic strategy employed has resulted in the development of three key\ntransformations: a photochem. Wolff rearrangement with tandem asym. ketene addn., a palladium-catalyzed\nC(sp )-H activation reaction of a cyclobutane substrate, and an inverse-electron demand hetero-Diels Alder\ncycloaddn. between a highly-oxidized ortho-quinone methide and a cyclohexanone-derived enol ether. This\nstrategy enables rapid assembly of the tricylic core of psiguadial B, with de novo construction of the transfused\ncyclobutane ring found in several natural products in this family. Current efforts directed toward\ndeveloping a successful cyclization reaction to form a highly strained seven-membered ring will also be\npresented.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/48336, title ="Natural product synthesis: A platform for discovery in chemistry and biology", author = "Reisman, Sarah E.", pages = "ORGN 776", month = "August", year = "2014", url = "https://resolver.caltech.edu/CaltechAUTHORS:20140811-145022145", note = "© 2014 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 lab. has ongoing research programs targeting the chem. syntheses of several natural products, including members of the epidithiodiketopiperazines, the ent-kauranoids, and the acutumine alkaloids. 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 our latest progress in both our methodol. and target-directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/42362, title ="Natural Product Synthesis: A Platform for Chemical Discovery", author = "Reisman, Sarah E.", pages = "WRM-262", month = "October", year = "2013", url = "https://resolver.caltech.edu/CaltechAUTHORS:20131112-080054809", note = "© 2013 American Chemical Society.", revision_no = "13", abstract = "Our laboratory has ongoing research programs targeting the chemical syntheses of several\nnatural products, including members of the epidithiodiketopiperazines, the ent-kauranoids, and\nthe acutumine alkaloids. The densely packed arrays of heteroatoms and stereogenic centers that\nconstitute these polycyclic targets challenge the limits of current synthetic methodology. This\nseminar will describe our latest progress in both our methodological and target-directed synthesis\nendeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/41893, title ="Award Address (Arthur C. Cope Scholar Awards (CSY) sponsored by Arthur C. Cope Fund). Natural product synthesis: A platform for chemical discovery", author = "Reisman, Sarah E.", pages = "ORGN-237", month = "September", year = "2013", url = "https://resolver.caltech.edu/CaltechAUTHORS:20131011-110722162", note = "© 2013 American Chemical Society.", revision_no = "11", abstract = "The overarching goal of the Reisman lab. is to discover, develop, and study new chem. reactions within the context of natural\nproduct total synthesis. The chem. synthesis of natural products enables the study of their biol. properties, and can provide\naccess to synthetic derivs. with improved therapeutic properties or that can serve as mechanistic probes. As importantly, these\nsynthetic undertakings serve to drive innovation in, and deepen our fundamental understanding of, org. and organometallic\nchem. Our lab. has ongoing research programs targeting the chem. syntheses of several natural products, including members of\nthe epidithiodiketopiperazines, the ent-kauranoids, and the acutumine alkaloids. The densely packed arrays of heteroatoms and\nstereogenic centers that constitute these polycyclic targets challenge the limits of current synthetic methodol. This seminar will\ndescribe our latest progress in both our methodol. and target-directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/43820, title ="Discoveries and diversions in natural product synthesis", author = "Reisman, Sarah E.", pages = "COMSCI-8", month = "September", year = "2013", url = "https://resolver.caltech.edu/CaltechAUTHORS:20140213-145722485", note = "© 2013 American Chemical Society.", revision_no = "12", abstract = "Our lab. seeks to discover, develop, and study new chem. reactions within the context of natural product total\nsynthesis. The chem. synthesis of natural products enables the study of their biol. properties, and can\nprovide access to synthetic derivs. with improved therapeutic properties or that can serve as mechanistic\nprobes. Importantly, these synthetic undertakings often highlight shortcomings of the existing state-of-the-art\nand inspire the discovery of new chem. Our lab. has ongoing research programs targeting the chem. syntheses\nof several natural products, including members of the epidithiodiketopiperazines, the ent-kauranoids, and the\nacutumine alkaloids. The densely packed arrays of heteroatoms and stereogenic centers that constitute these\npolycyclic targets challenge the limits of current synthetic methodol. This seminar will describe our latest\nprogress in both our methodol. and target-directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/41783, title ="Natural Product Synthesis: A Platform for Chemical Discovery", author = "Reisman, Sarah E.", pages = "NORM-12", month = "July", year = "2013", url = "https://resolver.caltech.edu/CaltechAUTHORS:20131009-085028526", note = "© 2013 American Chemical Society", revision_no = "11", abstract = "The overarching goal of our research is to discover, develop, and study new chem. reactions within the context of natural\nproduct total synthesis. The chem. synthesis of natural products enables the study of their biol. properties, and can provide\naccess to synthetic derivs. with improved therapeutic properties or that can serve as mechanistic probes. As importantly, these\nsynthetic undertakings serve to drive innovation in, and deepen our fundamental understanding of, org. and organometallic\nchem. Our lab. has ongoing research programs targeting the chem. syntheses of several natural products, including members of\nthe epidithiodiketopiperazines, the ent-kauranoids, and the acutumine alkaloids. The densely packed arrays of heteroatoms and\nstereogenic centers that constitute these polycyclic targets challenge the limits of current synthetic methodol. This seminar will\ndescribe our latest progress in both our methodol. and target-directed synthesis endeavors.", } @conference_item {CaltechAUTHORS_https://authors.library.caltech.edu/id/eprint/37849, title ="New methods and strategies for the enantioselective\nsynthesis of polycyclic natural products", author = "Reisman, Sarah E.", pages = "ORGN-473", month = "April", year = "2013", url = "https://resolver.caltech.edu/CaltechAUTHORS:20130410-101421544", revision_no = "11", abstract = "The overarching goal of the Reisman lab. is to discover, develop, and study new chem.\nreactions within the context of natural product total synthesis. The chem. synthesis of\nnatural products enables the study of their biol. mechanisms, and can provide access to\nsynthetic derivs. with improved therapeutic properties. As importantly, these synthetic\nundertakings serve to drive innovation in, and deepen our fundamental understanding of,\norg. and organometallic chem. This seminar will describe our latest progress in both our\nmethodol. and target-directed synthesis endeavors.", }