Kinetic control of proline amide rotamers:: Total synthesis of trans,trans- and cis,cis-ceratospongamide

被引：45

作者：

Deng, SJ ^{[1
]}

Taunton, J ^{[1
]}

机构：

[1] Univ Calif San Francisco, Dept Mol & Cellular Pharmacol, San Francisco, CA 94143 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 06期

关键词：

D O I：

10.1021/ja017160a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ceratospongamide is a cyclic peptide natural product that is biosynthesized as a mixture of two proline rotamers. Remarkably, these rotamers do not detectably interconvert at temperatures up to 100 °C. Here we report high-yielding syntheses of each rotamer and demonstrate that the threonine-derived oxazoline plays a critical role in determining the kinetic distribution of conformational isomers. Copyright © 2002 American Chemical Society.

引用

页码：916 / 917

页数：2

共 12 条

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