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Total synthesis of (+)-13-deoxytedanolide.

Authors
  • Smith, Amos B 3rd
  • Adams, Christopher M
  • Lodise Barbosa, Stephanie A
  • Degnan, Andrew P
Type
Published Article
Journal
Journal of the American Chemical Society
Publication Date
Jan 15, 2003
Volume
125
Issue
2
Pages
350–351
Identifiers
PMID: 12517144
Source
Medline
License
Unknown

Abstract

In this communication we describe the first total synthesis of (+)-13-deoxytedanolide, an architecturally complex marine macrolide possessing significant antitumor activity. The cornerstone of the synthesis comprises a highly convergent dithiane coupling used to construct the carbon skeleton, followed by a novel use of the Evans-Tishchenko reduction to oxidize the C(1) aldehyde to an ester in the presence of the oxidatively labile dithiane.

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