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Total synthesis of (+)-13-deoxytedanolide
Amos B Smith1, Christopher M Adams, Stephanie A Lodise Barbosa
1Department of Chemistry, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu
Journal of the American Chemical Society
|January 9, 2003
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.