Total synthesis of ent-25-hydroxycholesterol and other ent-sterols

Abstract: 25-Hydroxycholesterol plays multiple roles in lipid metabolism, antivirus process, inflammatory response, and cell survival. 25-hydroxycholesterol enantiomer, Ent-25-hydroxycholesterol, is an important compound to study and analyse for further insight and details into the mechanisms. Here, we report a novel and practical synthesis of highly pure ent-25-hydroxycholesterol. Moreover, this versatile synthetic route affords other five Ent-sterols, which include Ent-Testosterone, Ent-DHEA sulfate, Ent-DHEA, Ent-Androstenediol, and Ent-Androstenedione. Those Ent-sterols will be valuable tools to probe the lipid-protein interactions and their biological functions.