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Synthesis 2011(23): 3848-3858  
DOI: 10.1055/s-0031-1289570
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical Synthesis of (-)-Kainic Acid

Satoshi Takita, Satoshi Yokoshima, Tohru Fukuyama*
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Fax: +81(3)58028694; e-Mail: fukuyama@mol.f.u-tokyo.ac.jp;
Further Information

Publication History

Received 25 August 2011
Publication Date:
20 October 2011 (online)

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Abstract

A highly practical total synthesis of (-)-kainic acid has been accomplished. The synthesis features the stereoselective alkylation of an iodolactone intermediate efficiently prepared from (+)-carvone and introduction of carboxylic acid by hydrolysis of a nitrile accompanied by epimerization.

Key words

kainoids - iodolactone - Curtius rearrangement - stereoselective alkylation - total synthesis

1

Visiting researcher from KYORIN Pharmaceutical Co. Ltd.

10

For recent reviews, see: ref. 4.

17

The use of methyl or isopropyl bromoacetate as an alkylating reagent resulted in the concomitant alkylation of the product.

20

CCDC 817431 (16a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.