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DOI: 10.1055/s-0031-1289570
A Practical Synthesis of (-)-Kainic Acid
Publication History
Publication Date:
20 October 2011 (online)
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
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- Supporting Information
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References
Visiting researcher from KYORIN Pharmaceutical Co. Ltd.
10For recent reviews, see: ref. 4.
17The use of methyl or isopropyl bromoacetate as an alkylating reagent resulted in the concomitant alkylation of the product.
20CCDC 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.