Toward a General Route to the Eunicellin Diterpenes:  The Asymmetric Total Synthesis of Deacetoxyalcyonin Acetate

Gary A. Molander,* David J. St. Jean, Jr., and Julia Haas
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
J. Am. Chem. Soc., 2004, 126 (6), pp 1642–1643
DOI: 10.1021/ja0398464
Publication Date (Web): January 27, 2004
Copyright © 2004 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.

, gmolandr@sas.upenn.edu

Abstract

Abstract Image

A novel approach to the hydroisobenzofuran core utilizing a TiCl4-mediated [4+3] annulation is reported. This [4+3] annulation protocol provides a short, general route to the hydroisobenzofuran core present in the eunicellin diterpenes. Using this annulation, a short synthesis (17 steps) of deacetoxyalcyonin acetate, a member of the eunicellin family, has been achieved.

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History

  • Published In Issue February 18, 2004
  • Received November 28, 2003

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