Stereoselective Total Synthesis
of Leiocarpin C and (+)-Goniodiol

J. S. Yadav; V. Hari Krishna; A. Srilatha; R. Somaiah; B. V. Subba Reddy

doi:10.1055/s-0030-1257858

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Synthesis 2010(17): 3004-3012
DOI: 10.1055/s-0030-1257858

PAPER

Stereoselective Total Synthesis of Leiocarpin C and (+)-Goniodiol

J. S. Yadav*, V. Hari Krishna, A. Srilatha, R. Somaiah, B. V. Subba Reddy
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad - 500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;

Further Information

Publication History

Received 9 April 2010
Publication Date:
30 July 2010 (online)

Abstract
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Abstract

Total syntheses of styryl lactones, leiocarpin C and (+)-goniodiol have been accomplished in a highly stereoselective manner. The key steps involved in these syntheses are the Chan alkyne reduction, Sharpless asymmetric dihydroxylation, Horner-Wadsworth-Emmons olefination, aryl Grignard reaction, hydroboration, stereoselective alkoxy-directed keto-reduction, stereoselective 1,3-anti-allylation, esterification via ozonolysis, and intramolecular lactonization.

Key words

styryl lactones - dihydroxylation - olefination - hydroboration - 1,3-anti-allylation - ozonolysis

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