375348-84-8Relevant academic research and scientific papers
Lipase-Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer
Kadota, Kohei,Kurusu, Takashi,Taniguchi, Takahiko,Ogasawara, Kunio
, p. 618 - 623 (2001)
A synthesis of both enantiomers of levoglucosenone from acrolein dimer has been developed by employing lipase-mediated kinetic hydrolysis. Thus, acrolein dimer is transformed into racemic dihydrolevoglucosenone by sequential hydride reduction, oxidative acetalization, and Swern oxidation. Employing Saegusa-Larock conditions, dihydrolevoglucosenone is transformed into racemic levoglucosenone. The lipase-mediated resolution was best carried out under hydrolysis conditions with the endo-acetate generated from racemic levoglucosenone to give rise to highly enantioenriched (+)-alcohol and enantiopure (-)-acetate serving as the precursors of enantiopure levoglucosenone having the corresponding chirality.
