Stereodivergent approach to the asymmetric synthesis of bacillariolides: A formal synthesis of ent-bacillariolide IIGhosh, 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 Full text not archived in this repository. It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1021/ol061377y Abstract/SummaryAsymmetric 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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