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Stereoselective synthesis of the C1–C12 segment of iriomoteolide-1a: a very potent macrolide antitumor agent

✍ Scribed by Arun K. Ghosh; Hao Yuan

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
365 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A stereoselective synthesis of the C 1 -C 12 segment of the potent cytotoxic macrolide, iriomoteolide 1a, has been accomplished. The key steps involve an enzymatic kinetic resolution of a b-hydroxy amide, a Pd-catalyzed cross-coupling to construct a substituted allylsilane, a highly and stereoselective conjugate addition of lithium dimethylcopper to an a,b-acetylenic ester and an elaboration of the C 6 -C 7 trans-olefin geometry by a Julia-Kocienski olefination.

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