Isao Umezawa

Total synthesis of (-)-oudemansin X based on enzymatic resolution using immobilized lipase

Abstract (−)-Oudemansin X ( 1 ) was synthesized based on enzymatic resolution of (±)-diol 5 using immobilized lipase.

Lipase Catalyzed Resolution of (±)-2-Substituted 1-Propanol Derivatives Possessing an Aromatic Ring

For the purpose of the chiral synthesis of natural products, lipase-catalyzed kinetic resolutions of three types of 2-substituted 1-propanol derivatives (each having an aromatic ring) was investigated. In every case, chiral recognition of the primary alcohol unit took place to provide the corresponding alcohols and the acetates in high optical purity. The (2S,3S)-5-aryl-2-methyl-3-hydroxy-4E-pentenol 5 was formally converted into the antibiotic, (-)-oudemansin X.