Lipase-mediated synthesis of both enantiomers of levoglucosenone from acrolein dimer

A synthesis of both enantiomers of levoglucosenone from acrolein dimer has been developed by employing lipase-mediated kinetic hydrolysis. Thus, acrol ein dimer is transformed into racemic dihydrolevoglucosenone by sequential hydride reduction, oxidative acetalization, and Swern oxidation. Employing Saegusa-Larock conditions, dihydrolevoglucosenone is transformed into racem ic levoglucosenone. The lipase-mediated resolution was best carried out und er hydrolysis conditions with the endo-acetate generated from racemic levog lucosenone to give rise to highly enantioenriched (+)-alcohol and enantiopu re (-)-acetate serving as the precursors of enantiopure levoglucosenone hav ing the corresponding chirality.