Synthesis 2013; 45(6): 785-790
DOI: 10.1055/s-0032-1318303
paper
© Georg Thieme Verlag Stuttgart · New York

An Expeditious Enantiospecific Total Synthesis of (–)-Crassalactone C

Kavirayani R. Prasad*
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India   Email: prasad@orgchem.iisc.ernet.in
,
S. Mothish Kumar
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India   Email: prasad@orgchem.iisc.ernet.in
› Author Affiliations
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Publication History

Received: 31 December 2012

Accepted after revision: 31 January 2013

Publication Date:
21 February 2013 (online)


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Abstract

A concise and expeditious approach for the total synthesis of bioactive styryllactone (–)-crassalactone C is presented from tartaric acid. The main features of the synthesis include the desymmetrization of dimethylamide of tartaric acid and the effective use of cinnamoyl ester as a protecting group as well as a reactant in the ring-closing metathesis reaction.

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