Efficient synthesis of cholic acid derivates through stereoselective C-H functionalization from hyodeoxycholic acid

Publication date: Available online 15 February 2020Source: SteroidsAuthor(s): Yu-Yan Liang, Huan Huang, Yang Li, Rong-Kai Du, Jing Li, Yong-Hong Liu, Shan Li, Lei ZhangAbstractFive cholic acid derivatives (including allo-ω-muricholic acid and CDCA) were synthesized from hyodeoxycholic acid via selective oxidation of C3- or C6-hydroxyl groups by IBX and NBS oxidants and stereocontrolled conversion. The hydroxyl group could be introduced through hydrolyzing α-Br keto with K2CO3 aqueous solution or through oxidizing the double bond by monoperoxyphthalic acid. The reduction of C6-O6 carbonyl to methylene could undergo with PTSH, NaBH3CN and ZnCl2 only at 5β configuration. A feasible synthetic route of CDCA from HDCA has been established to avoid the epimerization with the yield of 45 % (8 steps). These strategies provided good yields, stereoselectivity and reproducibility for the preparation of cholic acid derivates and CDCA.Graphical abstract
Source: Steroids - Category: Drugs & Pharmacology Source Type: research