Synthesis of ursodeoxycholic acid from plant-source (20S)-21-hydroxy-20-methylpregn-4-en-3-one.

A straightforward and economical synthetic route for the preparation of ursodeoxycholic acid was developed from plant-source bisnoralcohol. • A facile route of producing ursodeoxycholic acid from plant-source BA is provided. • This promising route for production of ursodeoxycholic acid has a high yield. • This route of-fers a method for po-ten-tial large-scale pro-duc-tion of UDCA. A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from cheap and commercially available bisnoralcohol (BA). The key reaction conditions, including solvents, bases and reaction temperatures of the route were investigated and optimized. In the straightforward route for preparation of UDCA, most of the reaction steps have high conversions with average yields of 91%, and overall yield up to 59% (6 steps) from the plant-source BA. Especially in the last step of reduction and hydrolysis, there are five functional groups converted with calcd 97% per conversion in one-pot reaction. This promising route offers economical and efficient strategies for potential large-scale production of UDCA. [ABSTRACT FROM AUTHOR]