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

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[41] THE QUEEN RECOGNITION PHEROMONE OF SOLENOPSIS-INVICTA, PREPARATION OF (E)-6-(1-PENTENYL)-2H-PYRAN-2-ONE [J].