Stereocontrolled Total Synthesis of (−)-Kainic Acid

Hiroshi Sakaguchi,† Hidetoshi Tokuyama,‡ and Tohru Fukuyama*
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Org. Lett., 2007, 9 (9), pp 1635–1638
DOI: 10.1021/ol0631197
Publication Date (Web): March 30, 2007
Copyright © 2007 American Chemical Society
†

 Visiting researcher from Sumitomo Chemical Co., Ltd.

,
‡

 Current Address:  Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba, Sendai, 980-8578, Japan.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, fukuyama@mol.f.u-tokyo.ac.jp

Abstract

Abstract Image

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 α,β-unsaturated lactone with high diastereoselectivity. Two alternative protocols for the construction of the α,β-unsaturated lactone were also developed.

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History

  • Published In Issue April 26, 2007
  • Received December 25, 2006

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