Microbial reduction of varying size cyclic β-ketoesters.: Stereoselective synthesis of chiral lactones and epoxides

被引：5

作者：

Danchet, S ^{[1
]}

Buisson, D ^{[1
]}

Azerad, R ^{[1
]}

机构：

[1] Univ Paris 05, URA 400 CNRS, Chim & Biochim Pharmacol & Toxicol Lab, F-75270 Paris 06, France

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 1998年 / 5卷 / 1-4期

关键词：

1-cyclobutanol-2-carboxylate; beta-hydroxyester; omega-epoxyester; enantiospecificity; diastereoselectivity; dynamic kinetic resolution;

D O I：

10.1016/S1381-1177(98)00045-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The reduction of four- to eight-membered cyclic beta-ketoesters to the corresponding beta-hydroxyesters by various yeasts and fungi is described. The microbial reduction of ethyl cyclobutanone 2-carboxylate is reported for the first time. The different stereospecificities observed in these reductions involving a dynamic kinetic resolution are analysed. The enantiopure reduction products have been used in the synthesis of both enantiomers of functionalized lactones and epoxides. (C) 1998 Elsevier Science B.V. All rights reserved.

引用

页码：255 / 259

页数：5

共 9 条

[1] Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones [J].

Abalain, C ;

Buisson, D ;

Azerad, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2983-2996

[2]

AMICE P, 1974, B SOC CHIM FR I-PHYS, P1015

[3]

Buisson D., 1992, Biocatalysis, V5, P249, DOI 10.3109/10242429209014871

[4] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE MICROBIAL REDUCTION OF CYCLIC ALPHA-ALKYL BETA-KETOESTERS [J].

BUISSON, D ;

AZERAD, R .

TETRAHEDRON LETTERS, 1986, 27 (23) :2631-2634

[5] A FORMAL SYNTHESIS OF PTAQUILOSIN - THE AGLYCON OF A POTENT BRACKEN CARCINOGEN PTAQUILOSIDE [J].

COSSY, J ;

IBHI, S ;

KAHN, PH ;

TACCHINI, L .

TETRAHEDRON LETTERS, 1995, 36 (43) :7877-7880

[6] ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS BY YEAST .2. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES [J].

DEOL, BS ;

RIDLEY, DD ;

SIMPSON, GW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) :2459-2467

[7] CYCLIC SULFONE-3-CARBOXAMIDES AS NOVEL P-2-LIGANDS FOR RO-31-8959 BASED HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

THOMPSON, WJ ;

MUNSON, PM ;

LIU, WM ;

HUFF, JR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (01) :83-88

[8] ENANTIOSELECTIVE TOTAL SYNTHESES OF THE NITRARIA ALKALOIDS (-)-NITRAMINE AND (+)-ISONITRAMINE [J].

KEPPENS, M ;

DEKIMPE, N .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3916-3918

[9] ASYMMETRIC SYNTHESES OF (-)-MALYNGOLIDE AND (-)-FRONTALIN BY UTILIZING BAKERS-YEAST REDUCTION OF S-ETHYL 2-CYCLOPENTANONECARBOXYLTHIOATE [J].

SATO, T ;

MAENO, H ;

NORO, T ;

FUJISAWA, T .

CHEMISTRY LETTERS, 1988, (10) :1739-1742

← 1 →