ENANTIOSELECTIVE SYNTHESIS OF (S)-TRANS-GAMMA-BUTENYNYL GAMMA-AMINOBUTYRIC-ACID (GABA)

被引:15
作者
HOLMES, AB [1 ]
TABOR, AB [1 ]
BAKER, R [1 ]
机构
[1] MERCK SHARP & DOHME NEUROSCI RES CTR,HARLOW CM20 2QR,ESSEX,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期
关键词
D O I
10.1039/p19910003307
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective synthesis of (S)-trans-gamma-butenynyl gamma-aminobutyric acid (GABA) 1 by phthalimide displacement of the (R)-alcohol 9 (generated from the acetal 3) is reported. Novel hydride reductions of the pentadiynylic ether 3 to the trans-enyne 5 are reported and discussed.
引用
收藏
页码:3307 / 3313
页数:7
相关论文
共 24 条
[21]   ENANTIOSELECTIVE SYNTHESIS OF (S)-GAMMA-ACETYLENIC GAMMA-AMINOBUTYRIC ACID (GABA) AND (S)-TRANS-GAMMA-BUTENYNYL GABA [J].
TABOR, AB ;
HOLMES, AB ;
BAKER, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (15) :1025-1027
[22]  
TABOR AB, 1991, J CHEM SOC PERK T 1, P3307
[23]  
UCHIDA K, 1976, J ORG CHEM, V41, P2215, DOI 10.1021/jo00874a034
[24]   DIALKYLALUMINIUMHYDRIDE ALS STERISCH SPEZIFISCHE REDUKTIONSMITTEL FUR ACETYLENE [J].
WILKE, G ;
MULLER, H .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (02) :444-447