Research projects

Complementary and synergistic utilization of enzyme-catalyzed reactions and chemical transformation was studied, toward the efficient synthesis of complex target molecules involving valuable natural and unnatural products. The achievements are shown below. Lipase-catalyzed transesterification proceeded with specific site-selectivity contrasting to chemical transformations, and the syntheses of selinone and astringin, artepillin C became successful. It was revealed that the transesterification under non-aqueous conditions was advantageous for the substrates which are labile to water and/or prone to protonation under aqueous conditions. The preparation of highly enantiomerically pure (R)-3-hydroxy-N-methylpiperidine by the lipase-catalyzed kinetic resolution of corresponding racemate was established. The synthesis of enantiomers of NMB carboxylic acid was also successful, by discriminating he stereochemistry of remote chiral center in a primary acetate, as the key step.