Yeast-mediated synthesis of optically active diols with C-2-symmetry and (R)-4-pentanolide

被引：49

作者：

Ikeda, H ^{[1
]}

Sato, E ^{[1
]}

Sugai, T ^{[1
]}

Ohta, H ^{[1
]}

机构：

[1] KEIO UNIV,DEPT CHEM,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 24期

关键词：

D O I：

10.1016/0040-4020(96)00373-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-4-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：8113 / 8122

页数：10

相关论文

共 105 条

[21]

CERVINKA O, 1966, COLLECT CZECH CHEM C, V31, P2615

[22] BAKERS-YEAST REDUCTION OF 1,2-DIKETONES - PREPARATION OF PURE (S)-(-)-2-HYDROXY-1-PHENYL-1-PROPANONE [J].

CHENEVERT, R ;

THIBOUTOT, S .

CHEMISTRY LETTERS, 1988, (07) :1191-1192

[23] BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].

CSUK, R ;

GLANZER, BI .

CHEMICAL REVIEWS, 1991, 91 (01) :49-97

[24] USE OF BIOLOGICAL-SYSTEMS FOR THE PREPARATION OF CHIRAL MOLECULES .6. PREPARATION OF STEREOISOMERIC 2,4-DIOLS - SYNTHESIS AND CONFORMATIONAL STUDY OF BICYCLO DERIVATIVES, ISOMERIC COMPONENTS OF A PHEROMONE OF TRYPODENDRON-LINEATUM [J].

DAUPHIN, G ;

FAUVE, A ;

VESCHAMBRE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2238-2242

[25] PRODUCTION OF OPTICALLY-ACTIVE 2,3-BUTANEDIOL BY BACILLUS-POLYMYXA [J].

DEMAS, C ;

JANSEN, NB ;

TSAO, GT .

BIOTECHNOLOGY AND BIOENGINEERING, 1988, 31 (04) :366-377

[26] Combined microbial oxidation and reduction: A new approach to the high-yield synthesis of homochiral unsaturated secondary alcohols from racemates [J].

Fantin, G ;

Fogagnolo, M ;

Giovannini, PP ;

Medici, A ;

Pedrini, P .

TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :3047-3053

[27] Anti-Prelog microbial reduction of prochiral carbonyl compounds [J].

Fantin, G ;

Fogagnolo, M ;

Giovannini, PP ;

Medici, A ;

Pedrini, P ;

Gardini, F ;

Lanciotti, R .

TETRAHEDRON, 1996, 52 (10) :3547-3552

[28] USE OF BIOLOGICAL-SYSTEMS FOR THE PREPARATION OF CHIRAL MOLECULES .4. A 2-STEP CHEMOENZYMATIC SYNTHESIS OF A NATURAL PHEROMONE (4R,5S)-(-)-4-METHYL 5-HYDROXY HEPTAN 3-ONE, SITOPHILURE [J].

FAUVE, A ;

VESCHAMBRE, H .

TETRAHEDRON LETTERS, 1987, 28 (42) :5037-5040

[29] ELECTROCHEMICAL REDUCTION OF (+)-(2S,4S)-2,4-DIBROMOPENTANE [J].

FRY, AJ ;

BRITTON, WE .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (23) :4016-4021

[30] (2S,3S)-1-PHENYLTHIO-2,3-BUTANEDIOL - A USEFUL CHIRAL BUILDING BLOCK FOR A SIMPLE SYNTHESES OF (4R,5S)-5-HYDROXYHEXAN-4-OLIDE AND (4R,5S)-5-HYDROXY-2-HEXEN-4-OLIDE [J].

FUJISAWA, T ;

KOJIMA, E ;

SATO, T .

CHEMISTRY LETTERS, 1987, (11) :2227-2228

← 1 2 3 4 5 6 7 8 9 10 →