A chemoenzymatic strategy for the synthesis of enantiopure (R)-(-)-baclofen

被引：78

作者：

Mazzini, C ^{[1
]}

Lebreton, J ^{[1
]}

Alphand, V ^{[1
]}

Furstoss, R ^{[1
]}

机构：

[1] FAC SCI LUMINY,GRP BIOCATALYSE & CHIM FINE,CNRS,F-13288 MARSEILLE 9,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)00062-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A seven-step enantioselective synthesis of (R)-(-)-baclofen 1 is described The strategy developed involved as a Rey step, a microbiologically mediated Baeyer Villiger oxidation of the prochiral 3-(4'-chlorobenzyl)-cyclobutanone 3 which led to the optically pure (R)-(-)-4 lactone. This was further transformed throughout chemospecifle reactions into the target molecule (R)-(-)-1. (C) 1997, Published by Elsevier Science Ltd.

引用

页码：1195 / 1196

页数：2

共 11 条

[1] ALPHAND V, 1995, ENZYME CATALYSIS ORG, P745
[2] OXIDATION OF SOME PROCHIRAL 3-SUBSTITUTED CYCLOBUTANONES USING MONOOXYGENASE ENZYMES - A SINGLE-STEP METHOD FOR THE SYNTHESIS OF OPTICALLY ENRICHED 3-SUBSTITUTED GAMMA-LACTONES
GAGNON, R
GROGAN, G
GROUSSAIN, E
PEDRAGOSAMOREAU, S
RICHARDSON, PF
ROBERTS, SM
WILLETTS, AJ
ALPHAND, V
LEBRETON, J
FURSTOSS, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20): : 2527 - 2528
[3] BACLOFEN-H-3 AND H-3-GABA BIND TO BICUCULLINE-INSENSITIVE GABA-B SITES IN RAT-BRAIN
HILL, DR
BOWERY, NG
[J]. NATURE, 1981, 290 (5802) : 149 - 152
[4] IBUKA T, 1995, SYNTHETIC COMMUN, V25, P1777
[5] A PRACTICAL SYNTHESIS OF (2S,3R)-3-AMINO-2-METHYLPENTANOIC ACID FROM L-ASPARTIC ACID
JEFFORD, CW
MCNULTY, J
[J]. HELVETICA CHIMICA ACTA, 1994, 77 (08) : 2142 - 2146
[6] SYNTHESIS OF 9-[CIS-3-(HYDROXYMETHYL)CYCLOBUTYL]-ADENINE AND 9-[CIS-3-(HYDROXYMETHYL)CYCLOBUTYL]-GUANINE
KAIWAR, V
REESE, CB
GRAY, EJ
NEIDLE, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18): : 2281 - 2287
[7] GABA AGONISTS AND ANTAGONISTS
KERR, DIB
ONG, J
[J]. MEDICINAL RESEARCH REVIEWS, 1992, 12 (06) : 593 - 636
[8] A short chemoenzymatic synthesis of (+)-multifidene and (+)-viridiene
Lebreton, J
Alphand, V
Furstoss, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (07) : 1011 - 1014
[9] LEBRETON J, IN PRESS TETRAHEDRON
[10] Roberts E., 1986, BENZODIAZEPINES GABA, P1

← 1 2 →