Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies

被引：29

作者：

Benedetti, F ^{[1
]}

Forzato, C ^{[1
]}

Nitti, P ^{[1
]}

Pitacco, G ^{[1
]}

Valentin, E ^{[1
]}

Vicario, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(01)00059-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Both enantiomers of the diastereomeric cognac lactones have been synthesised using enzyme assisted reactions in the enantiodifferentiating step. This was accomplished by baker's yeast reduction of their precursors 3-methyl-4-oxononanoic acid and ester and by enzymatic hydrolysis of the latter. An inhibition of hydrolases by the products was observed. Trans-(+)-, trans-(-)-, cis-(+)- and cis-(-)-cognac lactones having 99, 88, 88 and 99% e.e., respectively, were thus obtained. Their CD spectra have also been studied. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：505 / 511

页数：7

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