研究简报

7β-羟基表雄酮的选择性合成

  • 黄燕敏 ,
  • 刘亮 ,
  • 戚斌斌 ,
  • 赵丹丹 ,
  • 杨雷 ,
  • 甘春芳 ,
  • 崔建国
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  • a 广西师范学院化学与生命科学学院 南宁 530001;
    b 四川万之药业股份有限公司 成都 610041

收稿日期: 2014-07-06

  修回日期: 2014-08-26

  网络出版日期: 2014-09-12

基金资助

广西教育厅自然科学重点基金(No. 201202ZD059)资助项目.

Selective Synthesis of 7β-Hydroxyepiandrosterone

  • Huang Yanmin ,
  • Liu Liang ,
  • Qi Binbin ,
  • Zhao Dandan ,
  • Yang Lei ,
  • Gan Chunfang ,
  • Cui Jianguo
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  • a College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001;
    b Sichuan Welltzpharm Inc., Chengdu 610041

Received date: 2014-07-06

  Revised date: 2014-08-26

  Online published: 2014-09-12

Supported by

Project supported by the Natural Science Fundation of Education Department of Guangxi Province (No. 201202ZD059).

摘要

7β-羟基表雄酮(4)是一种具有良好消炎功能的甾体化合物, 以去氢表雄酮为原料, 通过3-位羟基保护和Collin试剂氧化得到3-乙酰氧基-7-氧代去氢表雄酮(3), 然后化合物3在Ni2+离子存在条件下用NaBH4还原, 选择性地还原得到目标产物4, 同时得到其差向异构体7α-羟基表雄酮(5)及少量副产物7β-羟基去氢表雄酮(6), 同时对不同温度下还原反应的化学选择性及立体选择性进行了探索. 合成物结构经NMR及IR进行表征.

本文引用格式

黄燕敏 , 刘亮 , 戚斌斌 , 赵丹丹 , 杨雷 , 甘春芳 , 崔建国 . 7β-羟基表雄酮的选择性合成[J]. 有机化学, 2015 , 35(1) : 241 -245 . DOI: 10.6023/cjoc201407007

Abstract

The 7β-hydroxyepiandrosterone (4) is a kind of compound possessing strong anti-inflammatory properties. Using dehydroisoandrosterone as starting material, 3β-acetoxy-7-oxodehydroisoandrosterone (3) was obtained by acetylation and oxidization. In the presence of Ni2+, compound 3 was selectively reduced to give compound 4, its 7-epimer, 7α-hydroxyepi- androsterone (5) and byproduct 6. The condition of selective reduction was investigated further. The structures of all compounds were characterized by IR, NMR and MS techniques.

参考文献

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