Total Synthesis of Cytotoxic Macrolide Amphidinolide B<SUB>1</SUB> and the Proposed Structure of Amphidinolide B<SUB>2</SUB>

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J. Am. Chem. Soc., 130 (23), 7253–7255, 2008. 10.1021/ja803012n
Web Release Date: May 20, 2008

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

rich.carter@oregonstate.edu

Received April 23, 2008

Abstract:

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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