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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 9
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Original Articles

Improved Chiral Synthesis of Ravuconazole

, , &
Pages 1611-1625 | Received 08 Sep 2008, Published online: 02 Apr 2009
 

Abstract

A short, elegant, and high yielding synthesis of ravoconazole is presented. The key step of this synthesis is an enantioselective palladium-catalyzed chiral zinc-allene addition reaction. The starting materials are 2-chloro-1-(2,4-difluorophenyl)-ethanone and (R)-4-phenylbutyn-2-ol obtained from enzymatic resolution of its racemate.

ACKNOWLEDGMENTS

We are grateful for the important contribution of the analytical services of Basilea China, especially to Xianzheng Liang and Jianxia Zhou for the determinations of the ee of the produced compounds. Skillful technical assistance by other analytic chemists in Basilea China is greatly acknowledged.

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