Donald R. Deardorff, Department of Chemistry, Occidental College

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Presentation transcript:

Donald R. Deardorff, Department of Chemistry, Occidental College Strategy for the Enantioselective Preparation of Polyhydroxylated Pyrrolidines: Synthesis of DAB-1 and (-)-Anisomycin Donald R. Deardorff, Department of Chemistry, Occidental College The synthesis of naturally occurring (-)-coniine has been realized using the retrosynthetic strategy shown below. Yields are currently being optimized. Synthetic Highlights: 1) The (R)-cyanohydrin starting material was prepared in 70% yield (>99% ee) from 2-hexenal and HCN upon exposure to the almond enzyme oxynitrilase. 2) The nitrogen functionality was introduced stereo- and regioselectively in 89% yield (95% ee) via a novel palladium-catalyzed 1,3-substitutive chiral transfer reaction. 3) Cyclization of the acyclic diene was achieved using a Grubbs ring-closing metathesis (RCM) reaction. The piperidine ring was isolated in 70% yield.