Total Synthesis of (−)-2-epi-Peloruside A

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• 作者：Amos B. Smith ; ; Jason M. Cox ; Noriyuki Furuichi ; Craig S. Kenesky ; Junying Zheng ; Onur Atasoylu ; William M. Wuest
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：December 18, 2008
• 年：2008
• 卷：10
• 期：24
• 页码：5501-5504
• 全文大小：179K
• 年卷期：v.10,no.24(December 18, 2008)
• ISSN：1523-7052

文摘

A convergent synthesis of (−)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (−)-2-epi-peloruside A via an unexpected epimerization at C(2).