Quantitative and Stereospecific Dihydroxylations of Δ5-Steroids: A Green Synthesis of Plant Growth Hormone Intermediates

被引：10
|
作者：
Li, Tao
Li, Chunbao [1 ]
机构：
[1] Tianjin Univ, Dept Chem, Sch Sci, Tianjin 300072, Peoples R China
来源：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2013年 / 61卷 / 51期
关键词：
dihydroxylation; quantitative; stereospecific; Delta(5)-steroids; H2O2; BIOLOGICAL-ACTIVITY; HYDROGEN-PEROXIDE; OXIDATION; EPOXIDES; ALKENES; ACID; HYDROXYLATION; STEROIDS; BEARING; OLEFINS;
D O I：
10.1021/jf404633y
中图分类号：
S [农业科学];
学科分类号：
09 ;
摘要：
Dihydroxylated Delta(5)-steroids are key intermediates in preparing steroids bearing a 5 alpha-hydroxy-6-oxo moiety, which are plant growth hormones. Quantitative and stereospecific dihydroxylations of Delta(5)-steroids have been realized, using H2O2 catalyzed by KI and H2SO4 at 80 degrees C in aqueous dioxane. The workup consisted only of concentrating the solvents and filtering the products; no chromatography was needed. The reaction conditions tolerate various functional groups on the Delta(5)-steroids. A mechanism for this reaction is proposed and the reason that the reaction is quantitative and stereospecific is explained.
引用
收藏
页码：12522 / 12530
页数：9
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