13652-48-7Relevant academic research and scientific papers
Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol
Tanaka, Akira,Tokuyama, Takahito,Saito, Akiko,Oritani, Takayuki
, p. 2435 - 2437 (1998)
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)-cataIyzed 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. - Keywords: lipase; kinetic resolution; asymmetric acetylation; geosmin; musty odour component.
