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
收藏
页码：8149 / 8152
页数：4
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