A concise synthesis of (+)-deoxoprosophylline via Co(III)(salen)-catalyzed two stereocentered HKR of racemic azido epoxides

An efficient synthesis of (+)-deoxoprosophylline has been achieved in high optical purity (99% ee) from readily available cis-2-butene-1,4-diol. The strategy employs Co-catalyzed Hydrolytic Kinetic Resolution (HKR) of two stereocentered racemic azido epoxides and diastereoselective intramolecular reductive cyclization as key reactions.