Microbiological reductions of chromen-4-one derivatives

被引:17
作者
Besse, P [1 ]
Baziard-Mouysset, G
Boubekeur, K
Palvadeau, P
Veschambre, H
Payard, M
Mousset, G
机构
[1] Univ Blaise Pascal, Lab Synth Electrosynth & Etud Syst Interet Biol, CNRS, UMR 6504, F-63177 Clermont Ferrand, France
[2] Inst Mat Nantes, Lab Chim Solides, F-44072 Nantes 03, France
[3] Univ Toulouse 3, Fac Pharm, Dept Chim Pharmaceut, F-31062 Toulouse, France
关键词
D O I
10.1016/S0957-4166(99)00558-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
From the microbiological reductions of 2-acetyl or 2-benzoylchromen-4-one both enantiomers of the corresponding alcohols were obtained with high enantiomeric excess. The absolute configurations were determined directly by an X-ray structural determination. The results obtained showed that for most of the microorganisms tested, an inversion of the configuration of the alcohol occurred with the change of the substituent (methyl to phenyl group) in position 2, but also with the presence of a bromine atom in position 6 of the aromatic ring, positioned quite far from the prochiral centre. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4745 / 4754
页数:10
相关论文
共 20 条
[1]   CHEMOENZYMATIC SYNTHESIS OF CHIRAL BETA-AZIDOALCOHOLS - APPLICATION TO THE PREPARATION OF CHIRAL AZIRIDINES AND AMINOALCOHOLS [J].
BESSE, P ;
VESCHAMBRE, H ;
CHENEVERT, R ;
DICKMAN, M .
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1727-1744
[2]   Chemoenzymatic synthesis of α-halogeno-3-octanol and 4- or 5-nonanols.: Application to the preparation of chiral epoxides [J].
Besse, P ;
Sokoltchik, T ;
Veschambre, H .
TETRAHEDRON-ASYMMETRY, 1998, 9 (24) :4441-4457
[4]   STUDIES ON V-TRIAZOLES .7. ANTI-ALLERGIC 9-OXO-1H,9H-BENZOPYRANO[2,3-D]-V-TRIAZOLES [J].
BUCKLE, DR ;
OUTRED, DJ ;
ROCKELL, CJM ;
SMITH, H ;
SPICER, BA .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (02) :251-254
[5]  
BUCKLE DR, 1982, J CHEM SOC P1, V2, P627
[6]  
CASY AF, 1993, STERIC FACTOR MED CH
[7]   BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].
CSUK, R ;
GLANZER, BI .
CHEMICAL REVIEWS, 1991, 91 (01) :49-97
[8]   Yeast-mediated synthesis of optically active diols with C-2-symmetry and (R)-4-pentanolide [J].
Ikeda, H ;
Sato, E ;
Sugai, T ;
Ohta, H .
TETRAHEDRON, 1996, 52 (24) :8113-8122
[9]  
KERGOMARD A, 1978, TETRAHEDRON LETT, V52, P5197
[10]  
MOSANDL A, 1987, J HIGH RES CHROMATOG, P67