1. 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.