Synthesis of (−)-Ilimaquinone via a Radical Decarboxylation and Quinone Addition Reaction

Taotao Ling, Erwan Poupon, Erik J. Rueden, and Emmanuel A. Theodorakis*
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358
Org. Lett., 2002, 4 (5), pp 819–822
DOI: 10.1021/ol025501z
Publication Date (Web): February 12, 2002
Copyright © 2002 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.

, etheodor@ucsd.edu

Abstract

Abstract Image

A stereoselective synthesis of (−)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivative 8 with benzoquinone (9). Final functionalization of 7 to ilimaquinone (4) is achieved by exploring the electronic effects of the residual thiopyridyl group.

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History

  • Published In Issue March 07, 2002
  • Received January 1, 2002

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