Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2216-2219.DOI: 10.6023/cjoc201304031 Previous Articles     Next Articles

Notes

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 出版日期:2013-10-25 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 Online:2013-10-25 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).

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