Synthesis of Optically Active γ-Lactones with Lipase Catalyst

Journal of Oleo Science

Volumn 55, Issue 12, 2006, Pages 629-635

  Shimotori, Yasutaka ^a   Miyakoshi, Tetsuo ^a  

^a MEIJI UNIVERSITY   (Japan)

Author keywords

enantiomeric excess; lipase; N benzyl 4 hydroxyalkanamide; lactones

Indexed keywords

EID: 84981506014     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.55.629     Document Type: Article

References (12)

1. A. MOSANDL and C. GUNTHER, Stereoisomeric Flavor Compounds. 20. Structure and Properties of γ-Lactone Enantiomers, J. Agric. Food Chem., Vol. 37, 413–418 (1989).
2. E. GUICHARD, Chiral γ-Lactones, Key Compounds to Apricot Flavor, ACS Symp. Ser., Vol. 596, 258–267 (1995).
3. E. GUICHARD, A. KUSTERMANN and A. MOSANDL, Chiral Flavor Compounds from Apricots, Distribution of γ-Lactone Enantiomers and Stereodifferentiation of Dihydroactinidiolide Using Multi-Dimensional Gas Chromatography, J. Chromatogr., Vol. 498, 396–401 (1990).
4. J.H. TUMLINSON, M.G. KLEIN, R.E. DOOLITEL, T.L. LADD and A.T. PROVEAUX, Identification of the Female Japanese Beetle Sex Pheromone: Inhibition of Male Response by an Enantiomer, Science, Vol. 197, 789–792 (1997).
5. Y. NAOSHIMA, H. HASEGAWA and T. SAEKI, Synthesis of (R)-Enantiomers of 5-Hexadecanolide and 4-Decanolide, Pheromone of the Oriental Hornet and a Defensive Secretion of Rove Beetles, Employing Asymmetric Reduction with Immobilized Baker's Yeast, Agric. Biol. Chem., Vol. 51, 3417–3419 (1987).
6. A.L. GUTMAN and T. BRAVDO, Enzyme-Catalyzed Enantion-convergent Lactonization of γ-Hydroxy Diesters in Organic Solvents, J. Org. Chem., Vol. 54, 4263–4265 (1989).
7. A.L. GUTMAN, K. ZUOBI and T. BRAVDO, Lipase-catalyzed Preparation of Optically Active γ-Butyrolactones in Organic Solvents, J. Org. Chem., Vol. 55, 3546–3552 (1990).
8. T. SUGAI, S. OHSAWA, H. YAMADA and H. OHTA, Preparation of Enantiomerically Enriched Compounds Using Enzymes; 7. Synthesis of Japanese Beetle Pheromone Utilizing Lipase-Catalyzed Enantioselective Lactonization, Synthesis, Vol. 12, 1112–1114 (1990).
9. E. FUKUSAKI, S. SENDA, Y. NAKAZONO and T. OMATA, Lipase-catalyzed Kinetic Resolution of Methyl 4-Hydroxy-5-tetradecynoate and Its Application to a Facile Synthesis of Japanese Beetle Pheromone, Tetrahedron, Vol. 47, 6223–6230 (1991).
10. Y. TERAO, K. TSUJI, M. MURATA, K. ACHIWA, T. NISHIO, N. WATANABE and K. SETO, Facile Process for Enzymic Resolution of Racemic Alcohols, Chem. Pharm. Bull., Vol. 37, 1653–1655 (1989).
11. L. WENMING, X. DAVID, R. OLJAN and J. THOMAS, A Mild Method for Ring-Opening Aminolysis of Lactones, Tetrahedron Lett., Vol. 42, 2439–2441 (2001).
12. Y. MATSUMURA, T. ENDO, M. CHIBA, H. FUKAWA and Y. TERAO, Facile Synthesis of Optically Active γ-Lactones via Lipase-catalyzed Reaction of 4-Substituted 4-Hydroxybutyramides, Chem. Pharm. Bull., Vol. 48, 304–305 (2000).