A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)imidazoleglycerol

被引：11

作者：

Paz, MM ^{[1
]}

Correa, JF ^{[1
]}

Cabeza, MI ^{[1
]}

Sardina, FJ ^{[1
]}

机构：

[1] UNIV SANTIAGO COMPOSTELA,DEPT QUIM ORGAN,SANTIAGO COMPOSTE 15706,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(96)02138-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH(2))(2)CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9259 / 9262

页数：4

共 15 条

[1]

AMES BN, 1957, J BIOL CHEM, V228, P131

[2] CLEAVAGE OF N-ACYL OXAZOLIDONES [J].

DAMON, RE ;

COPPOLA, GM .

TETRAHEDRON LETTERS, 1990, 31 (20) :2849-2852

[3] AN EFFECTIVE CHIROSPECIFIC SYNTHESIS OF (+)-PILOCARPINE FROM L-ASPARTIC ACID [J].

DENER, JM ;

ZHANG, LH ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1159-1166

[4]

DIFFERDING E, 1991, SYNLETT, P187

[5] SYNTHESIS OF DIPHTHAMIDE - THE TARGET OF DIPHTHERIA-TOXIN CATALYZED ADP-RIBOSYLATION IN PROTEIN-SYNTHESIS ELONGATION FACTOR-II [J].

EVANS, DA ;

LUNDY, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1495-1496

[6] A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF VANCOMYCIN-RELATED ARYLGLYCINES BY ENOLATE AZIDATION [J].

EVANS, DA ;

EVRARD, DA ;

RYCHNOVSKY, SD ;

FRUH, T ;

WHITTINGHAM, WG ;

DEVRIES, KM .

TETRAHEDRON LETTERS, 1992, 33 (09) :1189-1192

[7] ASYMMETRIC OXYGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-HYDROXY CARBOXYLIC-ACID SYNTHONS [J].

EVANS, DA ;

MORRISSEY, MM ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4346-4348

[8] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[9] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS [J].

EVANS, DA ;

BRITTON, TC ;

DOROW, RL ;

DELLARIA, JF .

TETRAHEDRON, 1988, 44 (17) :5525-5540

[10] AMELIORATION OF THE CONJUGATE ADDITION CHEMISTRY OF ALPHA-ALKOXYCOPPER REAGENTS - APPLICATION TO THE STEREOSPECIFIC SYNTHESIS OF C-GLYCOSIDES [J].

HUTCHINSON, DK ;

FUCHS, PL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) :4930-4939

← 1 2 →