Stereodivergent Approach to the Asymmetric Synthesis of Bacillariolides:  A Formal Synthesis of ent-Bacillariolide II

Autor: Ghosh, Subrata, Sinha, Saikat, G. B. Drew, Michael
Zdroj: Organic Letters; August 2006, Vol. 8 Issue: 17 p3781-3784, 4p
Abstrakt: 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.
Databáze: Supplemental Index