Baker's yeast reduction of cyclic δ-ketoesters:: synthesis and chiroptical properties of condensed δ-lactones

被引：14

作者：

Forzato, C ^{[1
]}

Nitti, P ^{[1
]}

Pitacco, G ^{[1
]}

Valentin, E ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(99)00098-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure condensed delta-lactones have been prepared from the corresponding delta-ketoesters by the use of Saccharomyces cerevisiae. The reactions were not only highly enantioselective but also highly diastereoselective, provided the baker's yeast was preincubated at 50 degrees C for 30 min. Interestingly, and contrary to what is usually found, the use of nutrients inhibited the bioreductions. The relative configurational assignments have been made by means of NMR, while the absolute configurations and conformations of the lactone rings were attributed by means of CD studies. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1243 / 1254

页数：12

共 46 条

[1] ARISAWA M, 1985, PLANTA MED, V5, P348
[2] OPTICAL ROTATORY DISPERSION STUDIES .69. ABSOLUTE CONFIGURATION OF 2-METHYLCYCLOHEXANOLS AND SOME OBSERVATIONS ON A TWIST FORM IN CONFORMATIONAL EQUILIBRIUM OF 2-METHYLCYCLOHEXANONE
BEARD, C
TAO, RCC
ELLIOTT, T
DJERASSI, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) : 874 - &
[3] OPTICAL ROTATORY DISPERSION STUDIES .81. STEREOCHEMICAL STUDIES .27. CONFORMATIONAL DISTORTION IN 2-METHYLCYCLOHEXANONES
BEARD, C
SIPOS, F
DJERASSI, C
SICHER, J
TICHY, M
[J]. TETRAHEDRON, 1963, 19 (06) : 919 - &
[4] BEECHAM AF, 1968, TETRAHEDRON LETT, P3591
[5] BUCCIARELLI M, 1983, SYNTHESIS-STUTTGART, P897
[6] CARROLL FI, 1971, TETRAHEDRON LETT, P405
[7] CHEER CJ, 1976, TETRAHEDRON LETT, V43, P3877
[8] STEREOCHEMICAL STUDIES .10. SYNTHESIS OF SOME EPIMERIC DELTA-LACTONES
COOKE, E
PARADELLIS, TC
EDWARD, JT
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (01): : 29 - 34
[9] Cotarca L, 1997, SYNTHESIS-STUTTGART, P328
[10] COULOMBEAU C, 1971, B SOC CHIM FR, P516

← 1 2 3 4 5 →