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Tanaka A, Tokuyama T, Saito A, et al. Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol. Biosci Biotechnol Biochem. 1998;62(12):2435-7doi: 10.1271/bbb.62.2435.
Tanaka, A., Tokuyama, T., Saito, A., & Oritani, T. (1998). Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol. Bioscience, biotechnology, and biochemistry, 62(12), 2435-7. https://doi.org/10.1271/bbb.62.2435
Tanaka, A, et al. "Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol." Bioscience, biotechnology, and biochemistry vol. 62,12 (1998): 2435-7. doi: https://doi.org/10.1271/bbb.62.2435
Tanaka A, Tokuyama T, Saito A, Oritani T. Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol. Biosci Biotechnol Biochem. 1998;62(12):2435-7. doi: 10.1271/bbb.62.2435. PMID: 27392402.
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Biosci Biotechnol Biochem. 1998;62(12):2435-7. doi: 10.1271/bbb.62.2435.

Lipase-catalyzed Asymmetric Synthesis of Enantiomerically Pure (2S,4aS,8S)-4a,8-Dimethyl-2,3,4,4a,5,6,7,8-octahydro-2-naphthalenol.

Bioscience, biotechnology, and biochemistry

A Tanaka, T Tokuyama, A Saito, T Oritani

Affiliations

  1. a Division of Environmental Bioremediation, Graduate School of Agricultural Science, Tohoku University.
  2. b Division of Life Science, Graduate School of Agricultural Science, Tohoku University.

PMID: 27392402 DOI: 10.1271/bbb.62.2435

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.

Keywords: asymmetric acetylation; geosmin; kinetic resolution; lipase; musty odour component

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