An efficient synthesis of (R)-(-)-baclofen

被引：38

作者：

Resende, P

Almeida, WP

Coelho, F

机构：

[1] UNICAMP, Inst Quim, BR-13083970 Campinas, SP, Brazil

[2] Univ Paulista, Inst Ciencias Saude, Campinas, SP, Brazil

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 11期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/S0957-4166(99)00235-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

In this report we describe an efficient synthesis of (R)-(-)-baclofen, a selective GABA(B) agonist used as an antispastic agent. Our strategy is based on an enantioselective deprotonation of a cyclobutanone easily obtained by [2+2] cycloaddition of 4-chlorostyrene and dichloroketene. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2113 / 2118

页数：6

相关论文

共 35 条

[1] 3-THIENYLAMINOBUTYRIC AND 3-FURYLAMINOBUTYRIC ACIDS - SYNTHESIS AND BINDING GABA-B RECEPTOR STUDIES [J].

BERTHELOT, P ;

VACCHER, C ;

FLOUQUET, N ;

DEBAERT, M ;

LUYCKX, M ;

BRUNET, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2557-2560

[2]

BLOOM FE, 1996, GOODMAN GILMANS PHAR, P267

[3]

BORKA L, 1979, ACTA PHARM SUEC, V16, P345

[4] GABA-A AND GABA-B RECEPTOR-SITE DISTRIBUTION IN THE RAT CENTRAL-NERVOUS-SYSTEM [J].

BOWERY, NG ;

HUDSON, AL ;

PRICE, GW .

NEUROSCIENCE, 1987, 20 (02) :365-383

[5] BACLOFEN - 10 YEARS ON [J].

BOWERY, NG .

TRENDS IN PHARMACOLOGICAL SCIENCES, 1982, 3 (10) :400-403

[6]

BOWERY NG, 1990, GABAB RECEPTORS IN MAMMALIAN FUNCTION, P3

[7] HALOGENATED KETENES .I. DICHLOROKETENE [J].

BRADY, WT ;

LIDDELL, HG ;

VAUGHN, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02) :626-&

[8] Enantioselective synthesis of beta-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: application to the synthesis of (R)-(-)-baclofen [J].

Brenna, E ;

Caraccia, N ;

Fuganti, C ;

Fuganti, D ;

Grasselli, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3801-3805

[9] CHEMOENZYMATIC ENANTIOSELECTIVE SYNTHESIS OF BACLOFEN [J].

CHENEVERT, R ;

DESJARDINS, M .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (11) :2312-2317

[10] CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF BACLOFEN [J].

CHENEVERT, R ;

DESJARDINS, M .

TETRAHEDRON LETTERS, 1991, 32 (34) :4249-4250

← 1 2 3 4 →