Chemistry of vinyl sulfones.: Approach to novel conformationally restricted analogues of glutamic acid

被引：17
作者：
Díez, D
García, P
Marcos, IS
Garrido, NM
Basabe, P
Broughton, HB
Urones, JG
机构：
[1] Univ Salamanca, Fac Ciencias Quim, Dept Quim Organ, E-37008 Salamanca, Spain
[2] Lilly SA, Madrid 28108, Spain
来源：
TETRAHEDRON | 2005年 / 61卷 / 03期
关键词：
D O I：
10.1016/j.tet.2004.10.072
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A totally different approach to conformationally restricted glutamic acid analogues is described, in which one of the acid functions is replaced by a cyclopropanol. The reactivity of cyclopropanol vinyl sulfones toward addition of lithiated Schollkopf bislactim ether provides a facile synthesis of a-amino acid diastereoisomers. Conformational analysis of these analogues, incorporating solvation effects, and docking to a glutamate receptor model, are used to show the relevance of the conformational restrictions employed. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：699 / 707
页数：9
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