A chemoenzymatic preparation of both enantiomers of omega-hydroxymethyl-substitute lactones

被引：16

作者：

Buisson, D

Azerad, R

机构：

[1] Laboratoire de Chimie, Biochim. Pharmacologiques T., Univ. Rene Descartes-Paris V, 75270-Paris Cedex 06

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 01期

关键词：

D O I：

10.1016/0957-4166(95)00408-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(R)- and (S)-delta-hydroxymethyl vaterolactone and epsilon-hydroxymethyl caprolactone were prepared as tert-butyldiphenylsilyl derivatives, in good yields and high enantiomeric purities, in a 5 step sequence, starting from the microbial stereospecific reduction of ethyl 2-oxocyclopentane or 2-oxocyclohexane carboxylates respectively.

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页码：9 / 12

页数：4

相关论文

共 28 条

[1]

AZERAD R, 1992, NATO ASI SER, P421

[2] A NEW, ELEGANT ROUTE TO A KEY INTERMEDIATE FOR THE SYNTHESIS OF 9(O)-METHANOPROSTACYCLIN [J].

BARCO, A ;

BENETTI, S ;

POLLINI, GP ;

BARALDI, PG ;

GANDOLFI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4776-4778

[3] SYNTHETIC APPROACHES TO THE AVERMECTINS - STUDIES ON THE HEXAHYDROBENZOFURAN UNIT [J].

BARRETT, AGM ;

CAPPS, NK .

TETRAHEDRON LETTERS, 1986, 27 (46) :5571-5574

[4] MICROBIAL REDUCTION OF 1-TETRALONE 2-CARBOXYESTERS AS A SOURCE OF NEW ASYMMETRIC SYNTHONS [J].

BUISSON, D ;

CECCHI, R ;

LAFFITTE, JA ;

GUZZI, U ;

AZERAD, R .

TETRAHEDRON LETTERS, 1994, 35 (19) :3091-3094

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

BUISSON, D ;

AZERAD, R .

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

[6] TOTAL SYNTHESIS OF LEUKOTRIENE-B5 [J].

COREY, EJ ;

PYNE, SG ;

SU, W .

TETRAHEDRON LETTERS, 1983, 24 (45) :4883-4886

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

CSUK, R ;

GLANZER, BI .

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

[8] 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

[9]

Fr?ter G., 1980, HELV CHIM ACTA, V63, P1383

[10] THE STEREOSELECTIVE ALPHA-ALKYLATION OF CHIRAL BETA-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF [J].

FRATER, G ;

MULLER, U ;

GUNTHER, W .

TETRAHEDRON, 1984, 40 (08) :1269-1277