Synthesis of 16S,20S-Epoxypregnane-3S-ol Acetate and Its Regioselective Epoxide-opening Substitution

Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (19): 2272-2280. Previous Articles Next Articles

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16S,20S-环氧孕甾-3S-醇乙酸酯的合成及其区域选择性环氧开环取代反应

韩军¹，林静容*<^,1，金荣华¹，田伟生*^,1,2

(¹上海师范大学资源化学实验室上海 200234)
(²中国科学院上海有机化学研究所上海 200032)

投稿日期:2011-03-13 修回日期:2011-05-04 发布日期:2011-05-27
通讯作者: 林静容 E-mail:jrlin@shnu.edu.cn
基金资助:
上海市教育委员会科研创新项目;上海师范大学一般科研项目

Synthesis of 16S,20S-Epoxypregnane-3S-ol Acetate and Its Regioselective Epoxide-opening Substitution

Han Jun¹ Lin Jingrong*^,1 Jin Ronghua¹ Tian Weisheng*^,1,2

(¹Laboratory of Resource Chemistry, Shanghai Normal University, Shanghai 200234)
(²Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)

Received:2011-03-13 Revised:2011-05-04 Published:2011-05-27
Contact: LIN JingRong E-mail:jrlin@shnu.edu.cn
Supported by:
The project supported by Innovation Program of Shanghai Municipal Education Commission

A synthetic method of 16S,20S-epoxypregnane-3S-ol acetate (4b) from pregnane-3S,16S, 20S-triol was developed. Then the epoxide-opening reaction of 4b was investigated under different conditions. The research results showed that 16S,20S-epoxypregnane-3S-ol acetate was chemo-selectively converted into 20R-bromopregnane-3S,16S-diol diacetate, 20R-bromopregnane-3S,16S-diol-3-acetate, 20R-chloropregnane-3S,16S-diol diacetate, 20R-iodopregnane-3S,16S-diol-3-acetate and pregnane-3S, 16S,20R-triol-3-acetate. These results not only provided new synthetic intermediates for the syntheses of steroidal drugs and natural steroids, but also presented epoxide-opening methods of steroids with an asymmetric oxetane ring.

Key words: tigogenin, pregnane-3S,16S,20S-triol, 16S,20S-epoxypregnane-3S-ol acetate, epoxide-opening, synthesis

Cite this article

HAN Jun, LIN Jing-Rong, JIN Rong-Hua, TIAN Wei-Sheng. Synthesis of 16S,20S-Epoxypregnane-3S-ol Acetate and Its Regioselective Epoxide-opening Substitution[J]. Acta Chimica Sinica, 2011, 69(19): 2272-2280.

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16S,20S-环氧孕甾-3S-醇乙酸酯的合成及其区域选择性环氧开环取代反应

Synthesis of 16S,20S-Epoxypregnane-3S-ol Acetate and Its Regioselective Epoxide-opening Substitution

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