Chem. J. Chinese Universities ›› 2021, Vol. 42 ›› Issue (9): 2782.doi: 10.7503/cjcu20210277

• Organic Chemistry • Previous Articles     Next Articles

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)

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

CLC Number: 

TrendMD: