title: Simple approach to optically active drimane sesquiterpenes based on enzymatic resolution.
abstract: When the beta-acyloxy esters (+/-)-10 and (+/-)-11 were exposed to the lipase OF-360 from Candida rugosa or immobilized lipase OF-360 in a water-saturated organic solvent, the hydrolyzed product (8aS)-6 was obtained in high chemical (40%) and optical (> 99% ee) yields. The absolute structure of (8aS)-6 was confirmed by the fact that (8aS)-6 was converted into an authentic sample gamma-keto nitrile (8aS)-17. Treatment of the diol (+/-)-12 with isopropenyl acetate in the presence of the lipase Godo E-4 from Pseudomonas sp. provided the unchanged (8aR)-12 (89% ee) in 42% yield.
authors.affiliation: School of Pharmaceutical Science, Toha University, Chiba, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Akita
authors.forename: M
authors.initials: M
authors.lastname: Nozawa
authors.forename: Y
authors.initials: Y
authors.lastname: Futagami
authors.forename: M
authors.initials: M
authors.lastname: Miyamoto
authors.forename: C
authors.initials: C
authors.lastname: Saotome
mesh_terms: D000107:Acetylation; D002175:Candida / Q000201:enzymology; D004800:Enzymes, Immobilized; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000302:isolation & purification; D013237:Stereoisomerism
chemical_list: D004800:Enzymes, Immobilized; D012717:Sesquiterpenes; D008049:Lipase