Total Synthesis of Cytotoxic Macrolide Amphidinolide B1 and the Proposed Structure of Amphidinolide B2

Liang Lu, Wei Zhang and Rich G. Carter
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331
J. Am. Chem. Soc., 2008, 130 (23), pp 7253–7255
DOI: 10.1021/ja803012n
Publication Date (Web): May 20, 2008
Copyright © 2008 American Chemical Society

Abstract

Abstract Image

The first enantioselective total syntheses of cytotoxic macrolide amphidinolide B1 and the proposed structure for amphidinolide B2 have been accomplished. Key features of the syntheses include a diastereoselective aldol condensation, a spontaneous Wadsworth−Emmons macrocyclization and a directed epoxidation/elimination sequence.

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History

  • Published In Issue June 11, 2008
  • Article ASAPMay 20, 2008
  • Received: April 23, 2008

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