有机化学 ›› 2020, Vol. 40 ›› Issue (7): 2114-2119.DOI: 10.6023/cjoc202002008 上一篇    下一篇

研究简报

6α和6β-羟基去氧胆酸的合成

牛伟, 肖丹, 程航, 徐亮   

  1. 四川大学华西药学院 天然药物系暨教育部靶向药物重点实验室 成都 610041
  • 收稿日期:2020-02-07 修回日期:2020-04-21 发布日期:2020-05-11
  • 通讯作者: 徐亮 E-mail:liangxu@scu.edu.cn
  • 基金资助:
    国家自然科学基金(No.21871190)资助项目.

Synthesis of 6α- and 6β-Hydroxydeoxycholic Acid

Niu Wei, Xiao Dan, Cheng Hang, Xu Liang   

  1. Key Laboratory of Drug Targeting, Ministry of Education, Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu 610041
  • Received:2020-02-07 Revised:2020-04-21 Published:2020-05-11
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21871190).

6α和6β-羟基去氧胆酸[DCA-6α-ol(6)和DCA-6β-ol(7)]是新近鉴定的两个来自于人类肝脏的重要三级胆汁酸代谢产物.以胆酸(1)为起始原料经10步反应方便快捷地同时实现DCA-6α-ol(6)和DCA-6β-ol(7)的合成.路线涉及Mukaiyama羟醛缩合、臭氧裂解和SmI2促进的羰基邻位还原脱氧等关键反应.

关键词: 胆汁酸, 6α-羟基去氧胆酸, 6β-羟基去氧胆酸, 合成

6α- and 6β-hydroxydeoxycholic acids[DCA-6α-ol (6) and DCA-6β-ol (7)] are recently identified important tertiary bile acids derived from deoxycholic acid (3) in human liver. A rapid and robust synthesis of DCA-6α-ol (6) and DCA-6β-ol (7) from cholic acid (1) in 10 steps involing the key Mukaiyama aldol condensation, ozone oxidative cleavage and SmI2 promoted reductive deoxygenation was conducted.

Key words: bile acid, 6α-hydroxydeoxycholic acid, 6β-hydroxydeoxycholic acid, synthesis