高等学校化学学报 ›› 2021, Vol. 42 ›› Issue (9): 2782.doi: 10.7503/cjcu20210277

• 有机化学 • 上一篇    下一篇

由醋酸去氢表雄酮合成熊去氧胆酸

陈旺(), 胡代花, 刘格歌   

  1. 陕西理工大学生物科学与工程学院, 汉中 723000
  • 收稿日期:2021-04-25 出版日期:2021-09-10 发布日期:2021-06-02
  • 通讯作者: 陈旺 E-mail:chenwang@snut.edu.cn
  • 基金资助:
    陕西省教育厅重点实验室项目(20JS023);陕西省科技厅农业攻关项目(2021NY-154)

Synthesis of Ursodeoxycholic Acid from Dehydroiso-androsterone 3-Acetate

CHEN Wang(), HU Daihua, LIU Gege   

  1. School of Biological Science and Engineering,Shaanxi University of Technology,Hanzhong 723000,China
  • Received:2021-04-25 Online:2021-09-10 Published:2021-06-02
  • Contact: CHEN Wang E-mail:chenwang@snut.edu.cn
  • Supported by:
    the Programme of Key Laboratory Shaanxi Province Education Department, China(20JS023);the Programme of Key Project of Agricultural Science and Technology of Shaanxi Province, China(2021NY?154)

摘要:

探索了用植物源商业原料合成熊去氧胆酸的新方法. 以醋酸去氢表雄酮为原料, 以区域选择性烯丙位氧化、 Mistunbu反应和Luche还原为关键步骤, 通过9步反应, 以38.6%的总收率合成了熊去氧胆酸. 其中, 关键中间体4由化合物3经改进的烯丙位氧化反应以较高产率获得. 对关键的烯丙基氧化反应的条件进行了优化, 包括溶剂、 氧化剂和反应温度. 该方法原料易得、 产率较高, 并且有效地避免了动物源性原料的风险, 易于实现规模化合成, 因而具有较高的应用价值.

关键词: 熊去氧胆酸, 醋酸去氢表雄酮, Mitsunobu反应, Crabtree’s催化剂

Abstract:

A new method for the synthesis of ursodeoxycholic acid from commercial plant-source materials was developed. Ursodeoxycholic acid was synthesized from dehydroepiandrosterone 3-acetate in 9 steps through a regioselective allyl oxidationat, Mistunobu reaction and Luche reduction as the key steps, with an overall yield of 38.6%. The key intermediate 4 was prepared in good yield by improved allylic oxidation of compound 3. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. Since all starting materials are cost-effective, commercially available and effectively avoided the risk of animal derived raw materials, this promising synthetic route offers economical and efficient strategies for potential production of Ursodeoxycholic Acid.

Key words: Ursodeoxycholic acid, Dehydroisoandrosterone 3-acetate, Mitsunobu reaction, Crabtree’s catalyst

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