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Synfacts 2007(9): 0900-0900  
DOI: 10.1055/s-2007-968835
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Kainic Acid

Contributor(s): Philip Kocienski, Zofia Komsta
H. Sakaguchi, H. Tokuyama, T. Fukuyama*
The University of Tokyo, Japan
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

(-)-Kainic acid, isolated from the Japanese marine alga Digena simplex, has been used for stimulation of nerve cells and imitation of some neurological disease states. Key points of the synthesis are: (1) ring-closing metathesis of D and (2) formation of the pyrrolidine ring via highly diastereoselective intramolecular Michael addition (F → G).