Total synthesis of (+)-13-deoxytedanolide.
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.
Smith
Amos B
AB
Department of Chemistry, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu
Adams
Christopher M
CM
Lodise Barbosa
Stephanie A
SA
Degnan
Andrew P
AP
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry
C409106:13-deoxytedanolide; D000970:Antineoplastic Agents; D018942:Macrolides