Semi-synthetic Ursodeoxycholic Acid From Chenodeoxycholic Acid

Ursodeoxycholic acid is a widely used pharmaceutical which has a good clinical effect on the treatment of a variety of gallstone disease, liver disease and et al. The semi-synthesis studies on ursodeoxycholic acid are described in the dissertation, which includes two chapters as follows:In Chapter 1, the significant progress of synthesis of ursodeoxycholic acid over the past 60 years has been reviewed.In Chapter 2, a new route of semi-synthesis of ursodeoxycholic acid starting from chenodeoxycholic acid was put forward. Isophthaloyl chloride was used to protect the C3 hydroxyl group of chenodeoxycholic acid, affording diesters 4. Then, it was reacted with CH3SO2Cl, resulting in the inversion of configuration in the system of DBU/AcOH. The stereochemistry of ursodeoxycholic acid was founded by this way.