Total synthesis of anti-HIV agent chloropeptin I

被引：155

作者：

Deng, HB ^{[1
]}

Jung, JK ^{[1
]}

Liu, T ^{[1
]}

Kuntz, KW ^{[1
]}

Snapper, ML ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 30期

关键词：

D O I：

10.1021/ja030249r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent diastereo- and enantioselective total synthesis of anti-HIV agent chloropeptin I is reported. Important features of the total synthesis include: (1) the use of Ti-catalyzed cyanide addition to imines to prepare a requisite amino acid moiety, (2) the discovery of the positive effect of MeOH in the Cu-mediated biaryl ether formation to afford one of the two macrocyclic peptide moieties, and (3) the discovery of the positive influence of collidine in the diastereoselective Pd-mediated cross-coupling to result in efficient formation of another macrocycle within this medicinally important molecule. This key step is performed in the presence of four unprotected phenols, two of which reside on dichlorophenylglycines. Copyright © 2003 American Chemical Society.

引用

页码：9032 / 9034

页数：3

共 29 条

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