ENANTIOMERICALLY PURE BETA-GAMMA-EPOXYESTERS FROM BETA-HYDROXYLACTONES - SYNTHESIS OF BETA-HYDROXYESTERS AND (-)-GABOB

被引：48

作者：

LARCHEVEQUE, M

HENROT, S

机构：

[1] UPR 402 du CNRS, Ecole Normale Supérieure Laboratoire de Chimie, 75231 Paris Cedex 05

来源：

TETRAHEDRON | 1990年 / 46卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(01)86765-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of enantiomerically pure β,γ-epoxyesters was achieved by chemoselective opening of β-hydroxybutanolides with trimethylsilyliodide followed by cyclisation of the resulting iodohydrins with silver oxide. The reaction of these epoxyesters with lithio or magnesiocuprates afforded stereochemically pure α-substituted β-hydroxyesters. Alternatively, (-)-GABOB was synthesized in optically pure form from the iodohydrin 2'a. © 1990.

引用

页码：4277 / 4282

页数：6

共 48 条

[1] SYNTHESIS OF S-4-AMINO-3-HYDROXYBUTYRIC AND R-4-AMINO-3-HYDROXYBUTYRIC ACID (GABOB) AND S-CARNITINE AND R-CARNITINE FROM ARABINOSE OR ASCORBIC-ACID
BOCK, K
LUNDT, I
PEDERSEN, C
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (04): : 341 - 344
[2] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE MICROBIOLOGICAL REDUCTION OF 2-METHYL 3-OXOALKANOATES
BUISSON, D
SANNER, C
LARCHEVEQUE, M
AZERAD, R
[J]. TETRAHEDRON LETTERS, 1987, 28 (34) : 3939 - 3940
[3] NEW CHIRAL BUILDING-BLOCKS BY MICROBIAL ASYMMETRIC REDUCTION - A DIRECT ACCESS TO FUNCTIONALIZED 2R,3R-2-METHYL-3-HYDROXY AND 2S,3R-2-METHYL-3-HYDROXY BUTYRATE SYNTHONS
BUISSON, D
HENROT, S
LARCHEVEQUE, M
AZERAD, R
[J]. TETRAHEDRON LETTERS, 1987, 28 (42) : 5033 - 5036
[4] STEREOSELECTIVE METHYLATION OF BETA-HYDROXYLACTONE DIANIONS
CHAMBERLIN, AR
DEZUBE, M
[J]. TETRAHEDRON LETTERS, 1982, 23 (30) : 3055 - 3058
[5] REGIOSELECTIVE OPENINGS OF 2,3-EPOXY ACIDS WITH ORGANOCUPRATES
CHONG, JM
SHARPLESS, KB
[J]. TETRAHEDRON LETTERS, 1985, 26 (39) : 4683 - 4686
[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[7] THE STEREOSELECTIVE ALPHA-ALKYLATION OF CHIRAL BETA-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF
FRATER, G
MULLER, U
GUNTHER, W
[J]. TETRAHEDRON, 1984, 40 (08) : 1269 - 1277
[8] ON THE STERIC COURSE OF BAKER YEAST MEDIATED REDUCTION OF ALKYL 4-AZIDO-3-OXOBUTYRATE AND 4-BROMO-3-OXOBUTYRATE - SYNTHESIS OF (R)-CARNITIN AND (S)-CARNITIN
FUGANTI, C
GRASSELLI, P
CASATI, P
CARMENO, M
[J]. TETRAHEDRON LETTERS, 1985, 26 (01) : 101 - 104
[9] BIFUNCTIONAL CHIRAL SYNTHONS VIA BIOCHEMICAL METHODS .5. PREPARATION OF (S)-ETHYL HYDROGEN-3-HYDROXYGLUTARATE, KEY INTERMEDIATE TO (R)-4-AMINO-3-HYDROXYBUTYRIC ACID AND L-CARNITINE
GOPALAN, AS
SIH, CJ
[J]. TETRAHEDRON LETTERS, 1984, 25 (46) : 5235 - 5238
[10] AMINO-ACIDS AS CHIRAL SYNTHONS - PREPARATION OF ENANTIOMERICALLY PURE (R) AND (S) MALIC-ACIDS AND ITS APPLICATION TO THE SYNTHESIS OF 3-HYDROXY 4-BUTANOLIDE
HENROT, S
LARCHEVEQUE, M
PETIT, Y
[J]. SYNTHETIC COMMUNICATIONS, 1986, 16 (02) : 183 - 190

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