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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (06): 835-838. 上一篇    下一篇

研究论文

11β-羟基-16β-甲基-16α,17α-环丙烷基-孕甾-1,4-二烯-3,20-二酮的合成

杨冰，杨俊，翁玲玲* 郑虎   

  1. (四川大学华西药学院 成都 610041)
  • 收稿日期:2005-06-12 修回日期:2006-01-09 发布日期:2006-05-31

Synthesis of 11β-Hydroxy-16β-methyl-16α,17α-methylene- pregna-1,4-dien-3,20-dione

YANG Bing,YANG Jun,WENG Ling-Ling*,ZHENG Hu   

  1. (West China School of Pharmacy, Sichuan University, Chengdu 610041)
  • Received:2005-06-12 Revised:2006-01-09 Published:2006-05-31

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由泼尼松龙(Prednisolone)为原料, 经甲磺酰化、甲基化、脱水、两次1,3-偶极反应以及其后的两次热分解共7步反应, 以23.5%的总收率首次制得了11β-羟基-16β-甲基-16α,17α-环丙烷基-孕甾-1,4-二烯-3,20-二酮这一重要的潜在药物及化学中间体. 实验同时发现, 1,3-偶极反应及其之后的热分解反应具有高度的立体选择性和区域选择性. 这种立体选择性和区域选择性通过1H NMR数据加以了证明.

关键词: 药物中间体, 16α,17α-环丙烷基孕甾, 合成, 区域选择性, 1,3-偶极反应, 立体选择性, 热分解

11β-Hydroxy-16β-methyl-16α,17α-methylene-pregna-1,4-dien-3,20-dione, an im-portant chemical intermediate and excellent medicinal candidate, was prepared from prednisolone through 7 steps of methylsulfonylation, methylation, dehydration and double 1,3-dipolar reaction followed by double thermal decomposition with the total yield of 23.5%. The results showed that 1,3-dipolar reaction and ther-mal decomposition were highly regio- and stereo-selectivities proved by the data of 1H NMR.

Key words: medicinal intermediate, 1,3-dipolar reaction, stereoselectivity, synthesis, thermal decomposition, regioselectivity, 16α,17α-methylenepregnanes