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

页码：3307 / 3313

页数：7

共 24 条

[1] RESEARCHES ON ACETYLENIC COMPOUNDS .61. THE SYNTHESIS OF 3 POLYACETYLENIC ESTERS [J].

BELL, I ;

JONES, ERH ;

WHITING, MC .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (APR) :1313-1322

[2]

Cason J., 1955, ORG SYNTH, VIII, P169

[3] A NOVEL ROUTE TO ALLENYL FLUORIDES - SYNTHESIS OF 4-AMINO-7-FLUOROHEPTA-5,6-DIENOIC ACID, THE 1ST FLUOROALLENYL AMINO-ACID [J].

CASTELHANO, AL ;

KRANTZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3491-3493

[4] ALLENIC AMINO-ACIDS .1. SYNTHESIS OF GAMMA-ALLENIC GABA BY A NOVEL AZA-COPE REARRANGEMENT [J].

CASTELHANO, AL ;

KRANTZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1877-1879

[5]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[6]

COREY EJ, 1967, J AM CHEM SOC, V89, P4246

[7] ORGANOMETALLIC COMPOUNDS OF GROUP-3 .35. STEREOSPECIFIC REDUCTIVE ALKYLATION OF ACETYLENES BY SUCCESSIVE HYDRALUMINATION AND CARBODEMETALLATION [J].

EISCH, JJ ;

DAMASEVITZ, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2214-2215

[8] ORGANOMETALLIC COMPOUNDS OF GROUP III .19. REGIOSPECIFICITY AND STEREOCHEMISTRY IN HYDRALUMINATION OF UNSYMMETRICAL ACETYLENES - CONTROLLED CIS OR TRANS REDUCTION OF 1-ALKYNYL DERIVATIVES [J].

EISCH, JJ ;

FOXTON, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3520-&

[9] A NOVEL CARBON-CARBON BOND SCISSION AND ISOMERIZATION MECHANISM OF VINYLALUMINUM COMPOUNDS [J].

EISCH, JJ ;

KASKA, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2165-&

[10] ON THE DOUBLE-BOND ISOSTERE OF THE PEPTIDE-BOND - PREPARATION OF AN ENKEPHALIN ANALOG [J].

HANN, MM ;

SAMMES, PG ;

KENNEWELL, PD ;

TAYLOR, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :307-314

← 1 2 3 →