Formal Total Synthesis of (+)-Neopeltolide

被引：32

作者：

Athe, Sudhakar ^{[1
]}

Chandrasekhar, Balla ^{[1
]}

Roy, Saumya ^{[1
]}

Pradhan, Tapan Kumar ^{[1
]}

Ghosh, Subhash ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 21期

关键词：

STEREOSELECTIVE-SYNTHESIS; MACROLIDE (+)-NEOPELTOLIDE; BIOLOGICAL EVALUATION; KINETIC RESOLUTION; MACROLACTONE CORE; TERMINAL EPOXIDES; NEOPELTOLIDE; ANALOGS; EFFICIENT;

D O I：

10.1021/jo301425c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：9840 / 9845

页数：6

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