Total synthesis of salinosporamide A

被引：114

作者：

Endo, A

Danishefsky, SJ

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 23期

关键词：

D O I：

10.1021/ja0522783

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total synthesis of potent proteasome inhibitor salinosporamide A (1) has been accomplished, which features strictly substrate-controlled operations starting with the only chiral center of (R)-pyroglutamic acid. The consecutive quaternary carbons within 1 have been efficiently constructed by manipulation of two intramolecular reactions: (1) carbonate-mediated internal acylation of imidate ester (4 → 14) and (2) selenocyclization of aldehyde to exocyclic methylene group (5 → 18). Copyright © 2005 American Chemical Society.

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页码：8298 / 8299

页数：2

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