Stereodivergent approach to the asymmetric synthesis of bacillariolides: a formal synthesis of ent-bacillariolide II |
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Authors: | Ghosh Subrata Sinha Saikat Drew Michael G B |
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Institution: | Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India. ocsg@iacs.res.in |
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Abstract: | reaction: see text] 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. |
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