SYNTHESIS OF CONFORMATIONALLY RESTRICTED CHIRAL GAMMA-AMINOBUTYRIC-ACID (GABA) ANALOGS

被引：10

作者：

PAPAIOANNOU, D ^{[1
]}

STAVROPOULOS, G ^{[1
]}

SIVAS, M ^{[1
]}

BARLOS, K ^{[1
]}

FRANCIS, GW ^{[1
]}

AKSNES, DW ^{[1
]}

MAARTMANNMOE, K ^{[1
]}

机构：

[1] UNIV BERGEN,DEPT CHEM,N-5007 BERGEN,NORWAY

来源：

ACTA CHEMICA SCANDINAVICA | 1991年 / 45卷 / 01期

关键词：

D O I：

10.3891/acta.chem.scand.45-0099

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The epimeric (2S, 3S)- and (2R, 3S)-3-amino-2-(carboxymethyl)oxolanes have been synthesised from (S)-N-tritylhomoserine lactone. The lactone was first reduced with diisobutylaluminium hydride to a diastereomeric mixture of the corresponding lactols which underwent Wittig olefination to give methyl (4S)-(E)-6-hydroxy-4-tritylaminohex-2-enoate. Fluoride-ion induced ring-closure gave a mixture of (2S, 3S)- and (2R, 3S)-oxolanes. After chromatographic separation and deprotection these yielded the required products. Application of the initial reduction to the bicyclic cis-N-trityl-4-hydroxyproline lactone failed to provide the corresponding lactol mixture, although this could be obtained indirectly by way of the corresponding methyl ester. While the lactol did indeed undergo olefination to yield (2S, 4S)-4-hydroxy-2-[(E)-2-(methoxycarbonyl)]ethenyl-1-tritylpyrrolidine, this latter could not be cyclised.

引用

页码：99 / 104

页数：6

共 17 条

[1] SYNTHESIS OF NONPROTEINOGENIC AMINO-ACIDS .2. PREPARATION OF A SYNTHETIC EQUIVALENT OF THE GAMMA-ANION SYNTHON FOR ASYMMETRIC AMINO-ACID SYNTHESIS [J].