Total Synthesis and Stereochemical Assignment of Callyspongiolide

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• 作者：Jingjing Zhou ; Bowen Gao ; Zhengshuang Xu ; Tao Ye
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：June 8, 2016
• 年：2016
• 卷：138
• 期：22
• 页码：6948-6951
• 全文大小：385K
• 年卷期：0
• ISSN：1520-5126

文摘

Total synthesis of four callyspongiolide stereoisomers led to unambiguous assignment of relative and absolute stereochemistry of the natural product. Key features of the convergent, fully stereocontrolled route include the use of Krische allylation, Kiyooka Aldol reaction, Kociénski–Julia olefination, Still–Gennari olefination, Yamaguchi macrocyclization, and Sonogashira coupling reaction. Biological evaluation of the synthesized compounds against an array of cancer cells revealed that the stereochemistry of the macrolactone core played an important role.