title: Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol.
abstract: Enantiomerically pure (2S,4aS,8S)-(+)-4a,8-dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol (3), a key intermediate in the synthesis of natural geosmin (1), was prepared by enzymatic kinetic resolution. When racemic 3 was submitted to lipase (PS-30)-catalyzed asymmetric acetylation, employing vinyl acetate as the acyl donor, requisite product (+)-3 with a high enantiomeric excess was attained as the remaining alcohol. Recrystallization resulted in an enantiomerically pure sample.
authors.affiliation: a Division of Environmental Bioremediation, Graduate School of Agricultural Science, Tohoku University.
authors.forename: A
authors.initials: A
authors.lastname: Tanaka
authors.affiliation: b Division of Life Science, Graduate School of Agricultural Science, Tohoku University.
authors.forename: T
authors.initials: T
authors.lastname: Tokuyama
authors.affiliation: a Division of Environmental Bioremediation, Graduate School of Agricultural Science, Tohoku University.
authors.forename: A
authors.initials: A
authors.lastname: Saito
authors.affiliation: b Division of Life Science, Graduate School of Agricultural Science, Tohoku University.
authors.forename: T
authors.initials: T
authors.lastname: Oritani
keywords: asymmetric acetylation; geosmin; kinetic resolution; lipase; musty odour component