Chiral auxiliaries as docking/protecting groups in biohydroxylation: The hydroxylation of enantiopure spirooxazolidines derived from cyclopentanone using Beauveria bassiana ATCC 7159

European Journal of Organic Chemistry

Volumn , Issue 23, 2000, Pages 3835-3847

  De Raadt, Anna ^a   Fetz, Barbara ^a   Griengl, Herfried ^a   Klingler, Markus Florian ^a   Kopper, Irene ^a   Krenn, Birgit ^a   Münzer, Dieter Franz ^a   Ott, René Georg ^a   Plachota, Peter ^a   Weber, Hans Jörg ^a   Braunegg, Gerhard ^a   Mosler, Winfried ^b   Saf, Robert ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

Asymmetric synthesis; Biohydroxylation; Biotransformations; Chiral auxiliaries; Ketones

Indexed keywords

AMINOALCOHOL; CYCLOPENTENONE; OXAZOLIDINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; BEAUVERIA; CHEMICAL STRUCTURE; CHIRALITY; FERMENTATION; HYDROXYLATION; NONHUMAN; SYNTHESIS;

EID: 0033674514     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200012)2000:23<3835::AID-EJOC3835>3.0.CO;2-E     Document Type: Article

References (49)

1. [1a] D. H. R. Barton, Tetrahedron 1998, 54, 5805-5817.
2. [1b] D. H. R. Barton, D. Doller, Acc. Chem. Res. 1992, 25, 504-512.
3. [21 For recent examples of the chemical hydroxylation of saturated carbon atoms see: [2a] K. Matsunaka, T. Iwahama, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1999, 40, 2165-2168.
4. [2b] G. Asensio, R. Mello, M. E. Gonzalez-Nunez, G. Castellano, J. Corral, Angew. Chem. 1996, 108, 196-198.
5. [2c] L. C. Kao, A. Sen, J. Chem. Soc., Chem. Commun. 1991, 1242-1243.
6. [3a] K. Faber, Biotransformations in Organic Chemistry, 2nd ed., Springer-Verlag, Berlin, 1995.
7. [3b] S. M. Roberts, J. Chem. Soc., Perkin Trans 1 1999, 1-21.
8. [4a] H. L. Holland, Organic Synthesis with Oxidative Enzymes, VCH, New York, 1992, pp. 72-76;
9. For recent examples of biohydroxylation in organic synthesis see: - [4b] R. A. Johnson, M. E. Herr, H. C. Murray, C. G. Chidester, F. Han, J. Org. Chem. 1992, 57, 7209-7212.
10. [4c] C. R. Davis, R. A. Johnson, J. I. Cialdella, W. F. Ligeett, S. A. Mizsak, F. Han, V. P. Marshall, J. Org. Chem. 1997, 62, 2252-2254.
11. [4d] C. R. Davies, R. A. Johnson, J. I. Cialdella, W. F. Liggett, S. A. Mizsak, V. P. Marshall, J. Org. Chem. 1997, 62, 2244-2251.
12. [4e] S. J. Aitken, G. Grogan, C. S.-Y. Chow, N. J. Turner, S. L. Flitsch, J. Chem. Soc., Perkin Trans. 1 1998, 3365-3370.
13. [4f] W. Adam, Z. Lukacs, D. Harmsen, C. R. Saha-Möller, P. Schreier, J. Org. Chem. 2000, 65, 878-882.
14. R. A. Johnson, M. E. Herr, H. C. Murray, G. S. Fonken, J. Org. Chem. 1968, 33, 3217-3221.
15. R. Furtoss, A. Archelas, J. D. Fourneron, B. Vigne, Enzymes as Catalysts in Organic Synthesis (Ed.: M. P. Schneider), D. Reidel Publishing Company, 1986, pp. 361-370.
16. S. Peitz, D. Wolker, G. Haufe, Tetrahedron 1997, 53, 17067-17078.
17. A. Kergomard, M. F. Renard, H. Veschambre, J. Org. Chem. 1982, 47, 792-798.
18. G. Braunegg, A. de Raadt, S. Feichtenhofer, H. Griengl, I. Kopper, A. Lehmann, H. J. Weber, Angew. Chem. Int. Ed. 1999, 38, 2763-2766.
19. R. Furstoss, A. Archelas, J. D. Fourneron, B. Vigne, in: Organic Synthesis: an interdisciplinary challenge, IUPAC (Eds.: J. Streith, H. Prinzbach, G. Schill), Blackwell Scientific Publications, Oxford, 1985, pp. 215-226.
20. E. Sundby, R. Azerad, T. Anthonsen, Biotech. Lett. 1998, 20, 337-340.
21. [12a] A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Braunegg, I. Kopper, M. Kreiner, A. Zeiser, K. Kieslich, Tetrahedron: Asymmetry 1996, 7, 467-472.
22. [12b] A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Braunegg, I. Kopper, M. Kreiner, A. Zeiser, Tetrahedron: Asymmetry 1996, 7, 473-490.
23. [12c] A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, H. Weber, G. Braunegg, I. Kopper, M. Kreiner, A. Zeiser, Tetrahedron: Asymmetry 1996, 7, 491-496.
24. Unpublished results.
25. H. L. Holland, T. A. Morris, P. J. Nava, M. Zabic, Tetrahedron 1999, 55, 7441-7460.
26. H. F. Olivo, M. S. Hemenway, M. H. Gezginci, Tetrahedron Lett. 1998, 39, 1309-1312.
27. A. Archelas, J. D. Fourneron, R. Furstoss, J. Org. Chem. 1988, 53, 1797-1799.
28. S. Pietz, R. Fröhlich, G. Haufe, Tetrahedron 1997, 53, 17055-17066.
29. Unpublished results. A screening program was conducted with a number of ketones with various protecting/docking groups.
30. M. K. Klingler, Ph. D. Dissertation, Tech. Univ. of Graz, 1999. A screening program examining a number of different microorganisms was carried out. However, results superior to those found with Beauveria bassiana were not observed.
31. D. R. Kelly, C. J. Knowles, J. G. Mahdi, I. N. Taylor, M. A. Wright, J. Chem. Soc., Chem. Commun. 1995, 729-730.
32. L. Gaziola, U. Bornscheuer, R. D. Schmid, Enantiomer 1996, 1, 49-54.
33. H. Holland, Current Opinion in Chemical Biology 1999, 3, 22-27.
34. [23a] J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc., New York, 1995.
35. [23b] M. Nogradi, Stereoselective Synthesis VCH, Weinheim, 1995.
36. C. G. Rabiller, K. Königsberger, K. Faber, H. Griengl, Tetrahedron 1990, 46, 4231-4240.
37. E. Holmberg, E. Dahlen, T. Norin, K. Hult, Biocatalysis 1991, 4, 305-312.
38. E. J. Corey, G. Schmidt, Tetrahedron Lett. 1979, 10, 399-402.
39. Numbering of the functionalised N-benzoylated spirooxazolidines is shown below: (Chemical Equation Presented)
40. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, New York, 1991.
41. [9].
42. C. F. Palmer, B. Webb, S. Broad, S. Casson, R. McCague, A. J. Willetts, S. M. Roberts, Bioorg. Med. Chem. Lett. 1997, 7, 1299-1302.
43. Camphanoate derivative 15: (Chemical Equation Presented)
44. L. Stryer, Biochemie, 4th ed., Spektrum-der-Wissenschaft-Verlagsgellschaft, Heidelberg, 1987.
45. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford, 1988.
46. M. J. McKennon, A. I. Meyers, J. Org. Chem. 1993, 58, 3568-3571.
47. J. E. Saavedra, J. Org. Chem. 1985, 50, 2379-2380.
48. W. C. Krueger, R. A. Johnson, L. M. Pschigoda, J. Am. Chem. Soc. 1971, 93, 4865-4872. Compound 12 was prepared in the same manner as that described for the corresponding enantiomer.
49. T. H. Eberlein, F. G. West, R. W. Tester, J. Org. Chem. 1992, 57, 3479-3482.