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

Volumn 62, Issue 12, 1998, Pages 2435-2437

  Tanaka, Akira ^a   Tokuyama, Takahito ^a   Saito, Akiko ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric acetylation; Geosmin; Kinetic resolution; Lipase; Musty odour component

Indexed keywords

EID: 85009576648     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.62.2435     Document Type: Article

References (4)

1. Saito, A., Tanaka, A., and Oritani, T., A Practical Synthesis of Enantiomerically Pure (—)-Geosmin via Highly Diastereoselec-tive Reduction of (4aS,8S)-4a,8-Dimethyl-4,4a,5,6,7,8-hexa-hydro-2(3H)-naphthalenone. Tetrahedron: Asymmetry, 1, 2923-2928 (1996).
2. Revial, G., Asymmetric Michael-type Alkylation of Chiral Im-ines. Enantioselective Syntheses of (—)-Geosmin and Two Other Related Natural Terpenes, as well as enant-(+)-Geosmin. Tetrahedron Lett., 31, 4121-4124 (1989).
3. Saito, A., Tanaka, A., and Oritani, T., Highly Diastereoselective Reduction of Bicyclic and Steroidal Conjugated Enones with DIBAL in THF-DME. Synthetic Commun., 21,1969-1973 (1997).
4. Weingarten, H., Chupp, J. P., and White, W. A., Ketimine Syntheses. Use of Titanium Tetrachloride in a New Procedure for Their Preparation. J. Org. Chem., 32, 3246-3249 (1967).