Highly regio- and stereospecific hydroxylation of C-1 position of 2-deacetoxytaxinine J derivative with DMDO

被引：13
|
作者：
Horiguchi, T [1 ]
Cheng, Q [1 ]
Oritani, T [1 ]
机构：
[1] Tohoku Univ, Grad Sch Agr Sci, Lab Appl Bioorgan Chem, Aoba Ku, Sendai, Miyagi 981, Japan
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 20期
基金：
日本学术振兴会;
关键词：
taxoids; dioxiranes; hydroxylation; regiospecificity; stereospecificity; epoxides; epoxidation;
D O I：
10.1016/S0040-4039(00)00514-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple chemical oxidation of 2-deacetoxytaxinine J derivative 3 using an excess of dimethyldioxirane (DMDO) results in a highly regio- and stereospecific hydroxylation of the C-1 position to afford the 1 beta-hydroxy alpha-4(20)-epoxide 6 and 1 beta-hydroxy beta-4(20)-epoxide 7. A plausible mechanism of this reaction via 'insertion' is proposed. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3907 / 3910
页数：4
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