Optically active 6-acetyloxy-2H-pyran-3(6H)-one obtained by lipase catalyzed transesterification and esterification

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1655-1658

  Van Den Heuvel, Marco ^a   Cuiper, Agnes D ^a   Van Der Deen, Hanneke ^a   Kellogg, Richard M ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00155-X     Document Type: Article

References (27)

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3. 2. Ferrier, R.J.; Prasad, N. J. Chem. Soc. C. 1969, 570-575; Fraser-Reid, B. Acc. Chem. Res. 1985, 18, 347-354; Holder, N.L. Chem. Rev. 1982, 82, 287-332.
4. 2. Ferrier, R.J.; Prasad, N. J. Chem. Soc. C. 1969, 570-575; Fraser-Reid, B. Acc. Chem. Res. 1985, 18, 347-354; Holder, N.L. Chem. Rev. 1982, 82, 287-332.
5. 3. Achmatowicz Jr., O.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973-1996; Lefebvre, Y. Tetrahedron Lett. 1972, 133-136; Constantinou-Kokotou, V.; Kokotos, G.; Georgiadis, M.P. Liebigs Ann. Chem. 1991, 151-154.
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7. 3. Achmatowicz Jr., O.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973-1996; Lefebvre, Y. Tetrahedron Lett. 1972, 133-136; Constantinou-Kokotou, V.; Kokotos, G.; Georgiadis, M.P. Liebigs Ann. Chem. 1991, 151-154.
8. 4. Davies, H.G.; Green, R.H.; Kelly, D.R.; Roberts, S.M. Biotransformations in Preparative Organic Chemistry; Academic Press: New York, 1989; Wong, C.H.; Whitesides, G.M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, A Comprehensive Handbook; VCH: Weinheim, 1995.
9. 4. Davies, H.G.; Green, R.H.; Kelly, D.R.; Roberts, S.M. Biotransformations in Preparative Organic Chemistry; Academic Press: New York, 1989; Wong, C.H.; Whitesides, G.M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, A Comprehensive Handbook; VCH: Weinheim, 1995.
10. 4. Davies, H.G.; Green, R.H.; Kelly, D.R.; Roberts, S.M. Biotransformations in Preparative Organic Chemistry; Academic Press: New York, 1989; Wong, C.H.; Whitesides, G.M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, A Comprehensive Handbook; VCH: Weinheim, 1995.
11. 5. Deen, H. van der; Hof, R.P.; Oeveren, A. van; Feringa, B.L.; Kellogg, R.M. Tetrahedron Lett. 1994, 35, 8441-8444.
12. 6. Deen, H. van der; Cuiper, A.C.; Hof, R.P.; Oeveren, A. van; Feringa, B.L.; Kellogg, R.M. J. Am. Chem. Soc. 1996, 118, 3801-3803.
13. 7. Lipases A, AKG, AY, CE, D, G, GC, L, M, N, PLE-A, PS, and R are from Amano; lipase CC, Hog Pancreatine lipase, and Pig Pancreas lipase from Sigma; lipase CA from NOVO.
14. 2. The samples are then analyzed by GC for e.e. and conversion. With immobilized lipases (23% (w/w) on HSC) amounts are used that correspond to 10 mg of lipase.
15. 9. Chen, C.S.; Sih, C.J. Angew. Chem. Int. Ed. Engl. 1989, 28, 695-707.
16. 10. Bovara, R.; Carrera, G.; Ferrara, L.; Riva, S. Tetrahedron: Asymm. 1991, 2, 931-938.
17. 11. Fitzpatrick, P.A.; Klibanov, A.M. J. Am. Chem. Soc. 1991, 113, 3166-3171; Wang, Y.J.; Wang, F.F.; Sheu, J.Y.; Tsai, Y.C. Biotechnol. Bioeng. 1992, 39, 1128-1132; Secundo, F.; Riva, S.; Carrea, G. Tetrahedron: Asymm. 1992, 3, 267-280; Wescott, C.R.; Klibanov, A.M. J. Am. Chem. Soc. 1993, 115, 1629-1631; Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 122.
18. 11. Fitzpatrick, P.A.; Klibanov, A.M. J. Am. Chem. Soc. 1991, 113, 3166-3171; Wang, Y.J.; Wang, F.F.; Sheu, J.Y.; Tsai, Y.C. Biotechnol. Bioeng. 1992, 39, 1128-1132; Secundo, F.; Riva, S.; Carrea, G. Tetrahedron: Asymm. 1992, 3, 267-280; Wescott, C.R.; Klibanov, A.M. J. Am. Chem. Soc. 1993, 115, 1629-1631; Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 122.
19. 11. Fitzpatrick, P.A.; Klibanov, A.M. J. Am. Chem. Soc. 1991, 113, 3166-3171; Wang, Y.J.; Wang, F.F.; Sheu, J.Y.; Tsai, Y.C. Biotechnol. Bioeng. 1992, 39, 1128-1132; Secundo, F.; Riva, S.; Carrea, G. Tetrahedron: Asymm. 1992, 3, 267-280; Wescott, C.R.; Klibanov, A.M. J. Am. Chem. Soc. 1993, 115, 1629-1631; Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 122.
20. 11. Fitzpatrick, P.A.; Klibanov, A.M. J. Am. Chem. Soc. 1991, 113, 3166-3171; Wang, Y.J.; Wang, F.F.; Sheu, J.Y.; Tsai, Y.C. Biotechnol. Bioeng. 1992, 39, 1128-1132; Secundo, F.; Riva, S.; Carrea, G. Tetrahedron: Asymm. 1992, 3, 267-280; Wescott, C.R.; Klibanov, A.M. J. Am. Chem. Soc. 1993, 115, 1629-1631; Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 122.
21. 11. Fitzpatrick, P.A.; Klibanov, A.M. J. Am. Chem. Soc. 1991, 113, 3166-3171; Wang, Y.J.; Wang, F.F.; Sheu, J.Y.; Tsai, Y.C. Biotechnol. Bioeng. 1992, 39, 1128-1132; Secundo, F.; Riva, S.; Carrea, G. Tetrahedron: Asymm. 1992, 3, 267-280; Wescott, C.R.; Klibanov, A.M. J. Am. Chem. Soc. 1993, 115, 1629-1631; Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 122.
22. 12. As in reference 8, but now 5 equivalents of n-butanol are used in the solvents indicated in the entries of Table 2, except for entry 9.
23. 2. The samples are then analyzed by GC for e.e. and conversion. With immobilized lipases amounts are used that correspond to 10 mg of lipase.
24. 14. For recent examples see: ref. 6; Ward, R.S. Tetrahedron: Asymm. 1995, 6, 1475-1490; Brand, S.; Jones, M.F.; Rayner, C.M. Tetrahedron Lett. 1995, 36, 8493-8496.
25. 14. For recent examples see: ref. 6; Ward, R.S. Tetrahedron: Asymm. 1995, 6, 1475-1490; Brand, S.; Jones, M.F.; Rayner, C.M. Tetrahedron Lett. 1995, 36, 8493-8496.
26. 15. Weber, H.K.; Stecher, H.; Faber, K. Biotechnol. Lett. 1995, 17, 803-808.
27. 16. All new compounds showed spectroscopic and analytical data in accordance with the structures.