Stereodivergent approach to the asymmetric synthesis of bacillariolides: A formal synthesis of ent-bacillariolide II

Ghosh, S., Sinha, S. and Drew, M.G.B. (2006) Stereodivergent approach to the asymmetric synthesis of bacillariolides: A formal synthesis of ent-bacillariolide II. Organic Letters, 8 (17). pp. 3781-3784. ISSN 1523-7060 doi: 10.1021/ol061377y

Abstract/Summary

Asymmetric synthesis of densely functionalized bicyclic frameworks for entry into bacillariolides I/III and ent-bacillariolide II is reported. The key features are ring-closing metathesis of a pair of diastereomerically related dienes obtained through a stereodivergent route from a R-(+)-glyceraldehyde derivative, transformation of a nonstereoselective cyclopentene ester enolate alkylation process to a completely stereoselective one through alkylation of a bulky ester enolate with a bulky electrophile, and a remote silyloxymethyl group directed epoxidation.