Ghosh, Subrata ; Sinha, Saikat ; Drew, Michael 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
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol061377y
Related URL: http://dx.doi.org/10.1021/ol061377y
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 12265 |
| Deposited On: | 10 Nov 2010 05:02 |
| Last Modified: | 10 Nov 2010 05:02 |
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