Total Synthesis of Iejimalide B

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• 作者：Qingshou Chen ; Dirk Schweitzer ; John Kane ; V. Jo Davisson ; Paul Helquist
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：July 1, 2011
• 年：2011
• 卷：76
• 期：13
• 页码：5157-5169
• 全文大小：1164K
• 年卷期：v.76,no.13(July 1, 2011)
• ISSN：1520-6904

文摘

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鈥揔ocienski 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.