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Synfacts 2006(3): 0199-0199  
DOI: 10.1055/s-2006-931925
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Kainic Acid

Contributor(s): Philip Kocienski
Y. Morita, H. Tokuyama, T. Fukuyama*
University Of Tokyo, Japan
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Publikationsdatum:
21. Februar 2006 (online)

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Significance

(-)-Kainic acid is a neurotoxin and antihelmintic principle isolated from the red alga Digenea simplex. A noteworthy feature of the Fukuyama synthesis is the use of the (+)-Sparteine surrogate E to achieve the regio- and stereoselective lithiation-carboxylation of the pyrrolidine ring in D. For a recent approach to (-)-Kainic acid based on asymmetric deprotonation with(-)-Sparteine see: M. M. Martínez, D. Hoppe Eur. J. Org. Chem. 2005, 8, 1427-1442.