Synthesis of 7,6-fused bicyclic lactams for use as beta-turn mimics

被引：10

作者：

Morales, O ^{[1
]}

Seide, W ^{[1
]}

Watson, SE ^{[1
]}

机构：

[1] Long Isl Univ, Dept Chem & Biochem, Brooklyn, NY 11201 USA

来源：

SYNTHETIC COMMUNICATIONS | 2006年 / 36卷 / 07期

关键词：

beta-turn; peptidomimetic; non-natural amino acid synthesis; chiral pool;

D O I：

10.1080/00397910500466496

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved synthesis of the 7,6-fused bicyclic lactam is presented starting from readily available chiral starting materials. ( S)-allylglycine is protected as the phthalimide derivative and coupled with ( S)-2-amino-6-hydroxyhexanoic acid methyl ester. Oxidation of the hydroxyl group to the aldehyde followed by enamide synthesis and acyl iminium ion cyclization provide the bicyclic system as a single diastereomer in good overall yield.

引用

页码：965 / 973

页数：9

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