An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone

•A novel synthetic route of producing UDCA was developed from plant-source DHEA.•Most of the reactions have high conversions and overall yield to 35% for 8 steps. A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiand...

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Bibliographic Details
Published in:Steroids 2021-08, Vol.172, p.108870-108870, Article 108870
Main Authors: Chen, Wang, Hu, Daihua, Feng, Zili, Liu, Zhaopeng
Format: Article
Language:English
Subjects:
Dehydroepiandrosterone
Dehydroepiandrosterone - chemistry
Oxidants - chemistry
Oxidation-Reduction
Solvents
Synthesis
Ursodeoxycholic acid
Ursodeoxycholic Acid - chemical synthesis
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Summary:•A novel synthetic route of producing UDCA was developed from plant-source DHEA.•Most of the reactions have high conversions and overall yield to 35% for 8 steps. A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from plant-source dehydroepiandrosterone (DHEA), with a Mistunobu reaction and regioselective allyl oxidationat as the key steps. The reaction conditions of the key allyl oxidation reaction were also investigated and optimized, including solvent, oxidant and reaction temperature. In this novel route for the preparation of UDCA, most of the reaction steps have high conversions and overall yield up to 35% for 8 steps. 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 UDCA.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2021.108870