Asymmetric synthesis of FR165914: A novel β3-adrenergic agonist with a benzocycloheptene structure

The asymmetric synthesis of a novel β3-adrenergic agonist FR165194 is described. The critical steps involve preparation of an optically active amine via stereoselective reduction of a chiral imine prepared from α-methylbenzylamine and synthesis of a chiral epoxide via the Sharpless asymmetric dihydroxylation