Solid and solution phase synthesis of α-keto amides via azetidinone ring-opening:: Application to the synthesis of poststatin

被引：18

作者：

Khim, SK ^{[1
]}

Nuss, JM ^{[1
]}

机构：

[1] Chiron Corp, Emeryville, CA 94608 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

azetidinone; cleavage reactions; keto acids and derivatives; solid-phase synthesis;

D O I：

10.1016/S0040-4039(99)00079-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,3-Diethoxy-N-sulfonyl and carbamoyl azetidin-2-ones undergo efficient ring-opening reaction with various amine nucleophiles. Subsequent acid hydrolysis of the ketal moiety generated alpha-keto amides in excellent overall yields. The naturally occurring serine protease inhibitor poststatin was synthesized using this ring-opening reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1827 / 1830

页数：4

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