Total synthesis, assignment of absolute stereochemistry, and structural revision of chlorofusin

被引：42

作者：

Qian, Wen-Jian ^{[1
]}

Wei, Wan-Guo ^{[1
]}

Zhang, Yong-Xia ^{[1
]}

Yao, Zhu-Jun ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 20期

关键词：

D O I：

10.1021/ja072225g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of chlorofusin was accomplished in a convergent fashion. With all four unambiguous diastereomeric model chromophores as references, the absolute stereochemistry of the chlorofusin chromophore was determined and revised to be (4S,8R,9S) by H-1 NMR studies and asymmetric synthesis. This allows the complete structure of natural chlorofusin to be assigned for the first time. Enantioselective copper-mediated oxidation of 4, mild coupling of azaphilone 2 with the free amine-bearing cyclopeptide 3, and a one-pot three-step protocol for the final spiro-aminal formation were successfully achieved with high efficiency to yield the correct stereochemical product 1a.

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页码：6400 / +

页数：3

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