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有机化学
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有机化学 ›› 2013, Vol. 33 ›› Issue (10): 2216-2219.DOI: 10.6023/cjoc201304031 上一篇    下一篇

研究简报

由猪去氧胆酸合成异熊去氧胆酸的新方法

刘双, 汪钢强, 刘张坤, 汪秋安   

  1. 湖南大学化学化工学院 长沙 410082
  • 收稿日期:2013-04-20 修回日期:2013-06-25 发布日期:2013-07-03
  • 通讯作者: 汪秋安 E-mail:wangqa@hnu.edu.cn
  • 基金资助:

    国家基础科学人才培养基金(No. J1210040/J0104)和湖南省研究生科研创新(No. CX2012B160)资助项目

A Novel Synthetic Approach of Alloursodeoxycholic Acid from Hydeoxycholic Acid

Liu Shuang, Wang Gangqiang, Liu Zhangkun, Wang Qiuan   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2013-04-20 Revised:2013-06-25 Published:2013-07-03
  • Supported by:

    Project supported by the Personal Training Funds in National Basic Science of China (No. J1210040/J0104) and the Hunan Provincial Innovation Foundation for Postgraduate (No. CX2012B160).

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研究了异熊去氧胆酸的合成新方法. 以猪去氧胆酸为原料, 通过9步反应(总产率为25%), 高效地合成了异熊去氧胆酸. 合成路线中的关键中间体4是由化合物3经改进的烯丙位氧化以较高产率获得. 合成反应的关键步骤分别是化合物5在Mistunobu反应条件下的构型转化和α,β-不饱和羰基化合物6发生的立体选择性Luche还原. 所有合成化合物的结构已通过1H NMR, 13C NMR, MS和IR等波谱方法进行了确认. 该合成途径原料易得、总产率较高、后处理操作简便, 具有较高的应用价值.

关键词: 异熊去氧胆酸, 猪去氧胆酸, Mitsunobu构型反转, Luche还原, 合成

A novel and highly efficient synthetic approach of alloursodeoxycholic acid, starting from hydeoxycholic acid in 9 steps with overall yield 25%, was reported. The key intermediate 4 was prepared in good yield by improved allylic oxidation of 3. The critical steps to stereoselectively inverse the configuration of 5 and α,β-unsaturated carbonyl reduction of 6 were realized under Mistunobu coditions and Luche reduction respectively. The structures of all synthetic compounds were confirmed by 1H NMR, 13C NMR, MS and IR spectra. The synthetic approach has the advantages of easy availability of starting materials, highly stereoselective, easily work-up and good overall yield, so it has considerable practical value.

Key words: alloursodeoxycholic acid, hydeoxycholic acid, Mistunobu configuration inversion, Luche reduction, synthesis