Total Synthesis of Dolabelide D

Peter K. Park, Steven J. O'Malley, Darby R. Schmidt, and James L. Leighton*
Department of Chemistry, Columbia University, New York, New York 10027
J. Am. Chem. Soc., 2006, 128 (9), pp 2796–2797
DOI: 10.1021/ja058692k
Publication Date (Web): February 9, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, leighton@chem.columbia.edu

Abstract

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The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation−crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

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History

  • Published In Issue March 08, 2006
  • Received December 22, 2005

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