Efficient synthesis of polyfunctionalised enantiopure diazepanone scaffolds

被引：25

作者：

Monasson, Olivier ^{[1
]}

Ginisty, Maryon ^{[1
]}

Bertho, Gildas ^{[1
]}

Gravier-Pelletier, Christine ^{[1
]}

Le Merrer, Yves ^{[1
]}

机构：

[1] Univ Paris 05, Lab Chim & Biochim Pharmacol & Toxicol, CNRS, UMR 8601, F-75270 Paris 06, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 46期

关键词：

scaffolds; epoxide opening; lactonisation; lactamisation; translocase MraY;

D O I：

10.1016/j.tetlet.2007.09.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of polyfunctionalised enantiopure 1,4-diazepan-3-one scaffolds from L-serine derivatives and azidoepoxides readily available from either L-ascorbic or D-isoascorbic acid, allowing access to various configurations at chiral centres, is described. The key steps are the nucleophilic opening of the epoxide by the amine of serine followed by a lactonisation-lactamisation sequence. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8149 / 8152

页数：4

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