Abstract
The first total syntheses of the architecturally complex indole terpenes (−)-nodulisporic acids C and D and the first total synthesis of the polyketide nahuoic acid Ci(Bii) will be described. Central to both synthetic strategies comprise the use of late-stage large fragment unions. For the nodulisporic acids, the speaker and his collaborators enlist the establishment of a process-scale synthetic protocol for a common eastern hemisphere intermediate and a palladium catalyzed cross-coupling/indolization cascade tactic, leading to the composite multi-substituted indole core. For nahuoic acid Ci(Bii) highlights include a titanium-catalyzed asymmetric Diels–Alder reaction, a Type II Anion Relay Chemistry (ARC) tactic, and a strategic late-stage large fragment union via a Micalizio alkoxide-directed alkyne-alkene coupling.
About the speaker
Prof Amos B Smith III received his BS-MS combined degree from Bucknell University in 1966 and PhD from the Rockefeller University in 1972. He joined University of Pennsylvania as an Assistant Professor of Chemistry and Assistant Member of Department of Chemistry and the Monell Chemical Senses Center in 1973. He was then promoted to Associate Professor in 1973 and Professor in 1981. Since 1990, he has served as Rhodes-Thompson Professor of Chemistry.
Prof Smith focuses on three principle research areas: (A) development of innovative synthetic methods of wide application, (B) demonstration of the utility of these synthetic tactics for the rapid construction of architecturally complex natural and unnatural products having significant bio-regulatory properties, and (C) novel bioorganic/medicinal chemistry programs, including non-peptide peptidomimetics. He is most notable for his research in the total synthesis of complex natural product, as well as the chemistry of mammalian pheromones. He is currently served as the editorial board members of Journal of Organic Chemistry, Journal of Antibiotics and Chemical & Pharmaceutical Bulletin. He is also on the boards of directors of Organic Reactions and Organic Syntheses. Besides, he has been the founding Editor-in-Chief of Organic Letters (American Chemical Society) since 1999.
Prof Smith is an inaugural fellow of the American Chemical Society (2009), a member of the ESPCI International Scientific Council (2007), a fellow of the American Academy of Arts and Sciences (2006), and a fellow of the American Association for the Advancement of Science (2002). Besides, he is the recipient of the Allan R Day Award (2015), the Perkin Prize for Organic Chemistry (2015) and the Simonsen Medal (2008) from the Royal Society of Chemistry, the Paul Gassman Award (2014) and the William H Nichols Medal (2014) from the American Chemical Society.
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