Formal Total Synthesis of (+)-Neopeltolide

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• 作者：Sudhakar Athe ; Balla Chandrasekhar ; Saumya Roy ; Tapan Kumar Pradhan ; Subhash Ghosh
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：November 2, 2012
• 年：2012
• 卷：77
• 期：21
• 页码：9840-9845
• 全文大小：307K
• 年卷期：v.77,no.21(November 2, 2012)
• ISSN：1520-6904

文摘

This paper describes the formal total synthesis of (+)-neopeltolide, a cytotoxic macrolide isolated from the marine sponge Neopeltidae. The key features of the synthesis include an asymmetric Evans alkylation to fix the C9-methyl center, Jacobsen hydrolytic kinetic resolution of terminal epoxides followed by their regioselective opening to fix the stereocenters at the C11 and C13 positions, respectively, a Pd-catalyzed oxa-Michael reaction to construct the tetrahydropyran ring, and Yamaguchi macrolactonization to form the macrocyclic core of the molecule.