A novel method for the formation of 2-azocanones by lactone-to-lactam ring contraction of 2-oxonanones

被引：21

作者：

Derrer, S

Feeder, N

Teat, SJ

Davies, JE

Holmes, AB

机构：

[1] Univ Cambridge, Cambridge Ctr Mol Recognit, Chem Lab, Cambridge CB2 1EW, England

[2] SERC, Daresbury Lab, CLRC, Warrington WA4 4AD, Cheshire, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 50期

基金：

英国工程与自然科学研究理事会;

关键词：

lactamisation; medium-ring heterocycles; lactones; ring transformations;

D O I：

10.1016/S0040-4039(98)02093-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As part of a project evaluating medium-ring lactams as constrained peptidomimetics, a novel method for the formation of multisubstituted eight-membered lactams has been developed. N-Protected 7-amino-8-hydroxyoctenoic acids were cyclised to give 8-amino-5,6-dehydro-2-oxocanones which underwent clean intramolecular O-to-N-acyl (lactone-to-lactam) ring contraction to yield 8-hydroxymethyl-6,7-dehydro-2-azocanones, suitable for elaboration to eight-membered lactam dipeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9309 / 9312

页数：4

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