ENANTIOSELECTIVE ESTERIFICATION OF 5-HYDROXY-2-METHYL-6-(DIETHOXYMETHYL)-1-CYCLOHEXENECARBALDEHYDE - SYNTHESIS OF BOTH ENANTIOMERS OF 6-METHYLBICYCLO[4.1.0]HEPT-2-ENE-1,2-DICARBALDEHYDE

被引：5

作者：

GUSTAFSSON, J

SANDSTROM, J

STERNER, O

机构：

[1] LUND UNIV,DIV ORGAN CHEM 2,S-22100 LUND,SWEDEN

[2] LUND UNIV,DIV ORGAN CHEM 1,S-22100 LUND,SWEDEN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 02期

关键词：

D O I：

10.1016/0957-4166(95)00043-O

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Racemic 5-hydroxy-2-methyl-6-(diethoxymethyl)-1-cyclohexenecarbaldehyde [(+/-)-5] was resolved by enantioselective transesterification with vinyl acetate in cyclohexane catalysed by lipase from Candida antarctica. The absolute stereochemistry of the acetate obtained was determined by CD technique. The products were used to synthesise both enantiomers of 6-methylbicyclo[4.1 .0]hept-2-ene-1,2-dicarbaldehyde (7), an analogue of the bioactive sesquiterpene isovelleral (1). The mutagenic activity of the three dialdehydes in the Ames' Salmonella/microsome assay is compared.

引用

页码：595 / 602

页数：8

共 23 条

[1] METHODS FOR DETECTING CARCINOGENS AND MUTAGENS WITH SALMONELLA-MAMMALIAN-MICROSOME MUTAGENICITY TEST [J].