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J Org Chem. 2011 Jul 1;76(13):5157-69. doi: 10.1021/jo200514m. Epub 2011 Apr 20.

Total synthesis of iejimalide B.

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  • 1Department of Chemistry and Biochemistry and Harper Cancer Research Center, University of Notre Dame, Notre Dame, Indiana 46556, United States.

Abstract

Iejimalide B, a structurally unique 24-membered polyene macrolide having a previously underutilized mode of anticancer activity, was synthesized according to a strategy employing Julia-Kocienski olefinations, a palladium-catalyzed Heck reaction, a palladium-catalyzed Marshall propargylation, a Keck-type esterification, and a palladium-catalyzed macrolide-forming, intramolecular Stille coupling of a highly complex cyclization substrate. The overall synthesis is efficient (19.5% overall yield for 15 linear steps) and allows for more practical scaled-up synthesis than previously reported strategies that differed in the order of assembly of key subunits and in the method of macrocyclization. The present synthesis paves the way for efficient preparation of analogues for drug development efforts.

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