Total Syntheses of (+)-Acutiphycin and (+)-trans-20,21-Didehydroacutiphycin

Amos B. Smith, III,* Sean S.-Y. Chen, Frances C. Nelson, Janice M. Reichert, and Brian A. Salvatore
Contribution from the Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104
J. Am. Chem. Soc., 1997, 119 (45), pp 10935–10946
DOI: 10.1021/ja972497r
Publication Date (Web): November 12, 1997
Copyright © 1997 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.

Abstract

The first total syntheses of the cytotoxic macrolides (+)-acutiphycin (1) and (+)-trans-20,21-didehydroacutiphycin (2) have been achieved. An acyclic stereocontrol strategy was employed to establish the configurations at C(5), C(10), and C(13) as well as the E geometry of the C(8,9)-trisubstituted olefin. Importantly, the natural source of 1 and 2, the blue-green alga Osillatoria acutissima, no longer produces these metabolites.

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History

  • Published In Issue November 12, 1997
  • Received July 23, 1997

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