Chemoenzymatic synthesis of (S)-2-cyanopiperidine, a key intermediate in the route to (S)-pipecolic acid and 2-substituted piperidine alkaloids

Tetrahedron Asymmetry

Volumn 9, Issue 9, 1998, Pages 1597-1604

  Nazabadioko, Serge ^a   Pérez, Ramón J ^a   Brieva, Rosario ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYANOPIPERIDINE; ALKALOID; PIPECOLIC ACID; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROMETRY; LIGAND BINDING; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0345310065     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00140-2     Document Type: Article

References (46)

1. (a) Strunz, G. M.; Findlay, J. A. Pyridine and Piperidine Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp. 89.
2. (b) Fodor, G. B.; Colasati, B. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 3, p. 1.
3. (c) Numata, A.; Ibuka, I. Alkaloids from Ants and Other Insects. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, pp. 193.
4. (d) Pinder, A. R. Nat. Prod. Rep. 1992, 9, 17.
5. (e) Ibid. 491-504.
6. (f) Wuonola, M. A. Org. Prep. Proced. Int. 1992, 583.
7. (g) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581.
8. (h) Harrison, T. Cont. Org. Synth. 1995, 2, 209. Ibid. 1996, 3, 259.
9. (h) Harrison, T. Cont. Org. Synth. 1995, 2, 209. Ibid. 1996, 3, 259.
10. (a) Norton, T. R.; Benson, A. A.; Seibert, R. A.; Bergstrom, F. W. J. Am. Chem. Soc. 1946, 68, 1330.
11. (b) Banitt, E. H.; Conard G. J. J. Labelled Compd. and Radiopharm. 1981, 28, 713.
12. (c) Becchietti, V.; Signorini, M.; Giordani, A. Eur. Pat. appl. EP 260, 041, 1988, (Chem. Abstr. 1988, 109, 92801g).
13. (c) Becchietti, V.; Signorini, M.; Giordani, A. Eur. Pat. appl. EP 260, 041, 1988, (Chem. Abstr. 1988, 109, 92801g).
14. (d) Terada, A.; Iizuka, Y.; Wachi, K.; Fujibayashi, K. Eur. Pat. Appl. EP 356, 247, 1990. (Chem. Abstr. 1990, 113, 78419g).
15. (d) Terada, A.; Iizuka, Y.; Wachi, K.; Fujibayashi, K. Eur. Pat. Appl. EP 356, 247, 1990. (Chem. Abstr. 1990, 113, 78419g).
16. (a) Froelich, O.; Bonin, M.; Quirion, J.-C.; Husson, H.-P. Tetrahedron: Asymmetry 1993, 4, 2335.
17. (b) Asami, M.; Usui, K.; Higuchi, S.; Inoue, S. Chem. Lett. 1994, 60, 297.
18. (c) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098.
19. (c) Asami, M.; Usui, K.; Higuchi, S.; Inoue, S. Chem. Lett. 1994, 60, 297.
20. Froelich, O.; Desos P.; Bonin, M.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1996, 61, 6700.
21. Perumattam, J.; Shearer, B. G.; Confer, W. L.; Mathew, R. M. Tetrahedron Lett. 1991, 32, 7183.
22. For recent synthesis of coniine, see: (a) Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047. (b) Moody, C. J.; Lighfot, A. P.; Gallagher, P. T. J. Org. Chem. 1997, 62, 746 and references cited therein. (c) Weymann, H.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151.
23. For recent synthesis of coniine, see: (a) Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047. (b) Moody, C. J.; Lighfot, A. P.; Gallagher, P. T. J. Org. Chem. 1997, 62, 746 and references cited therein. (c) Weymann, H.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151.
24. For recent synthesis of coniine, see: (a) Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047. (b) Moody, C. J.; Lighfot, A. P.; Gallagher, P. T. J. Org. Chem. 1997, 62, 746 and references cited therein. (c) Weymann, H.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151.
25. For asymmetric synthesis of pipecolic acid, see: (a) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769. (b) Fernández-García, C.; McKervey, A. Tetrahedron: Asymmetry, 1995, 6, 2905. For resolution of pipecolic acid, see: (c) Hardtman, G. E.; Houlihan, W. J.; Giger, A. US Patent, 4,760,065, Jul. 26, 1988. (Chem. Abstr. 1987, 107, 236730s). (d) Ng-Youn Chem. M. C.; Serreqi, A. N.; Huang, Q.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 2075.
26. For asymmetric synthesis of pipecolic acid, see: (a) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769. (b) Fernández-García, C.; McKervey, A. Tetrahedron: Asymmetry, 1995, 6, 2905. For resolution of pipecolic acid, see: (c) Hardtman, G. E.; Houlihan, W. J.; Giger, A. US Patent, 4,760,065, Jul. 26, 1988. (Chem. Abstr. 1987, 107, 236730s). (d) Ng-Youn Chem. M. C.; Serreqi, A. N.; Huang, Q.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 2075.
27. For asymmetric synthesis of pipecolic acid, see: (a) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769. (b) Fernández-García, C.; McKervey, A. Tetrahedron: Asymmetry, 1995, 6, 2905. For resolution of pipecolic acid, see: (c) Hardtman, G. E.; Houlihan, W. J.; Giger, A. US Patent, 4,760,065, Jul. 26, 1988. (Chem. Abstr. 1987, 107, 236730s). (d) Ng-Youn Chem. M. C.; Serreqi, A. N.; Huang, Q.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 2075.
28. For asymmetric synthesis of pipecolic acid, see: (a) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769. (b) Fernández-García, C.; McKervey, A. Tetrahedron: Asymmetry, 1995, 6, 2905. For resolution of pipecolic acid, see: (c) Hardtman, G. E.; Houlihan, W. J.; Giger, A. US Patent, 4,760,065, Jul. 26, 1988. (Chem. Abstr. 1987, 107, 236730s). (d) Ng-Youn Chem. M. C.; Serreqi, A. N.; Huang, Q.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 2075.
29. For asymmetric synthesis of pipecolic acid, see: (a) Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994, 59, 3769. (b) Fernández-García, C.; McKervey, A. Tetrahedron: Asymmetry, 1995, 6, 2905. For resolution of pipecolic acid, see: (c) Hardtman, G. E.; Houlihan, W. J.; Giger, A. US Patent, 4,760,065, Jul. 26, 1988. (Chem. Abstr. 1987, 107, 236730s). Ng-Youn Chem. M. C.; Serreqi, A. N.; Huang, Q.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 2075.
30. Copeland, T. D.; Wondrak, E. M.; Tozser, J.; Roberts M. M.; Oroszlan, S. Biochem. Biophys. Res. Commun. 1990, 169, 310.
31. Af Ekenstam, B. T.; Bovin C. US Patent 4695576, 1987. (Chem. Abstr. 1988, 108, 57228n).
32. Af Ekenstam, B. T.; Bovin C. US Patent 4695576, 1987. (Chem. Abstr. 1988, 108, 57228n).
33. (a) Kikumoto, R.; Tamao, Y.; Tezuka, T.; Tonomura, S.; Hara, H.; Ninomiya, K.; Hijikata, A.; Okamoto, S.; Biochemistry, 1984, 23, 85.
34. (b) Flynn, G. A.; Giruox, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914.
35. Smith III, A. B.; Condon, S. M.; McCauley, J. A.; Leazer Jr., J. L.; Leahy, J. W.; Maleczka Jr., R. E. J. Am. Chem. Soc. 1997, 119, 962.
36. Ireland, R. E. Gleason; J. L.; Gegnas, L. D.; Highsmith, T. K. J. Org. Chem. 1996, 61, 5856.
37. Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629.
38. (a) Effenberger, F. Angew. Chem. Int. Ed. Eng. 1994, 33, 1555.
39. (b) North, M. Synlett. 1993, 807.
40. (c) Kanerva, L. T. Acta Chem. Scand. 1996, 50, 234.
41. (a) Effenberger, F.; Jäger J. 1997, 62, 3867 and references cited therein. (b) Effenberger, F.; Jäger, J.; Chem. Eur. J. 1997, 3, 1370.
42. (a) Effenberger, F.; Jäger J. 1997, 62, 3867 and references cited therein. (b) Effenberger, F.; Jäger, J.; Chem. Eur. J. 1997, 3, 1370.
43. Menéndez, E.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1995, 989.
44. Effenberger, F.; Burkard, U.; Willfahrt, J. Liebigs Ann. Chem. 1986, 314.
45. Gerrier, L.; Royer, J.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754.
46. Hockless, D. C. R.; Mayadunne, R. C.; Wild, S. B.; Tetrahedron: Asymmetry 1995, 6, 3031.