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Org Lett. 2007 Apr 26;9(9):1635-8. Epub 2007 Mar 30.

Stereocontrolled total synthesis of (-)-kainic acid.

Author information

1
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Abstract

[reaction: see text] A stereocontrolled total synthesis of (-)-kainic acid is described. A fully functionalized trisubstituted pyrrolidine ring was constructed by ring-closing metathesis of an acrylate derivative followed by an intramolecular Michael addition of the resultant alpha,beta-unsaturated lactone with high diastereoselectivity. Two alternative protocols for the construction of the alpha,beta-unsaturated lactone were also developed.

PMID:
17394345
DOI:
10.1021/ol0631197
[Indexed for MEDLINE]

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