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Synthesis 2009(18): 3157-3161  
DOI: 10.1055/s-0029-1216938
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of Xestodecalactone C from l-Malic Acid

J. S. Yadav*, Y. Gopala Rao, K. Ravindar, B. V. Subba Reddy, A. V. Narsaiah
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 19 December 2008
Publication Date:
14 August 2009 (online)

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Abstract

An efficient total synthesis of the ten-membered macrolide, xestodecalactone C is described. The synthetic sequence uses Barbier-allylation, LiAlH4/LiI-mediated syn-stereoselective 1,3-asymmetric reduction, and intramolecular Friedel-Crafts acylation as key steps.

Key words

xestodecalactone C - Barbier allylation - stereoselective reduction - intramolecular Friedel-Crafts acylation

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