有机化学 ›› 2015, Vol. 35 ›› Issue (1): 241-245.DOI: 10.6023/cjoc201407007 上一篇    下一篇

研究简报

7β-羟基表雄酮的选择性合成

黄燕敏a, 刘亮b, 戚斌斌a, 赵丹丹a, 杨雷a, 甘春芳a, 崔建国a   

  1. 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 出版日期:2015-01-25 发布日期:2014-09-12
  • 通讯作者: 崔建国 E-mail:cuijg1954@126.com
  • 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 Yanmina, Liu Liangb, Qi Binbina, Zhao Dandana, Yang Leia, Gan Chunfanga, Cui Jianguoa   

  1. a College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001;
    b Sichuan Welltzpharm Inc., Chengdu 610041
  • Received:2014-07-06 Revised:2014-08-26 Online:2015-01-25 Published:2014-09-12
  • Supported by:

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

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.

关键词: 去氢表雄酮, 7β-羟基表雄酮, 7α-羟基表雄酮, 选择性还原

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.

Key words: dehydroisoandrosterone, 7β-epiandrosterone, 7α-epiandrosterone, selective reduction