A general strategy for the synthesis of azapeptidomimetic lactams

被引：24

作者：

Broadrup, RL ^{[1
]}

Wang, B ^{[1
]}

Malachowski, WP ^{[1
]}

机构：

[1] Bryn Mawr Coll, Dept Chem, Rosemont, PA 19010 USA

来源：

TETRAHEDRON | 2005年 / 61卷 / 43期

基金：

美国国家科学基金会;

关键词：

peptidomimetic; lactams; azapeptide; mitsunobu reaction;

D O I：

10.1016/j.tet.2005.08.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：10277 / 10284

页数：8

共 62 条

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