Enzymatic desymmetrization/resolution of epoxydiols derived from 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone

被引:12
作者
Betts, RL [1 ]
Murphy, ST [1 ]
Johnson, CR [1 ]
机构
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tetasy.2004.07.051
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The enzymatic desymmetrization/resolution of epoxydiols generated from the basic epoxidation and reduction of 1,4-naphthoquoinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone is described. 2,3-Epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol and 5,8-diallyloxy-2,3-epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol were desymmetrized in the presence of isopropenyl acetate using Burholderia cepacia lipase and Candida antartica lipase B, respectively. An enzymatic resolution of 8-benzyloxy-2,3-epoxy-1(alpha),2(alpha),3(alpha),4(alpha)-tetrahydronaphthalene-1,4-diol using B. cepacia lipase in isopropenyl acetate is also described. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2853 / 2860
页数:8
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