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

页码：3907 / 3910

页数：4

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