Diastereoselective synthesis of nonracemic 2-alkyl-5-hydroxypiperidines with (2R,5S)-configuration via a tandem wittig [2+3] cycloaddition reaction. Synthesis of epi-pseudoconhydrine and and homologs

Synthesis

Volumn , Issue 12, 1997, Pages 1405-1410

  Herdeis, Claus ^a   Schiffer, Thomas ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Cycloaddition reaction; Tandem reaction; Wittig reaction

Indexed keywords

CIS 2 ALKYL 5 HYDROXYPIPERIDINE; EPI PSEUDOCONHYDRINE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; STEREOCHEMISTRY;

EID: 0031450714     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1366     Document Type: Article

References (64)

1. For recent syntheses of β-hydroxypiperidines in general, see: Paterne, M.; Dhal, R.; Brown, E. Bull. Chem. Soc. Jpn. 1989, 62, 1321.
2. Jung, M.E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528.
3. Knight, D.W.; Lewis, N.; Share, A.C.; Haigh, D. Tetrahedron: Asymmetry 1993, 4, 625.
4. Zhao, S.; Ghosh, A.; D'Andrea, S.V.; Freeman, J.P.; v. Voigtländer, P.F.; Carter, D.B.; Smith, M.W.; Blinn, J.R.; Szmuszkovicz, J. Heterocycles 1994, 39, 163.
5. Boudreault, N.; Ball, R.G.; Bayly, C.; Bernstein, M.A.; Leblanc, Y. Tetrahedron 1994, 50, 7947.
6. Ward, A.D.; Cooper, M.A. Tetrahedron Lett. 1994, 35, 5065.
7. Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943.
8. Cossy, J.; Dumas, C.; Michel, P.; Pardo, D.G. Tetrahedron Lett. 1995, 36, 549.
9. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715.
10. Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4001.
11. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467.
12. Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molius, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 2501.
13. De Kimpe, N.; Boelens, M.; Contreras, J. Tetrahedron Lett. 1996, 37, 3171.
14. Burgess, L.E.; Gross, E.K.M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255.
15. Toyooka, N.; Yotsui, Y.; Yoshida, Y.; Momose, T. J. Org. Chem. 1996, 61, 4882.
16. Wilken, J.; Kossenjans, M.; Saak, W.; Haase, D.; Pohl, S.; Martens, J. Liebigs Ann. Chem. 1997, 573.
17. Oetting, J.; Holzkamp, J.; Meyer, H.H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477.
18. For reviews on piperidine alkaloids, see: (a) Daly, J. W. Proc. Natl. Acad. Sci. USA 1995, 92, 9.
19. (b) Hammann, P. Nachr. Chem. Tech. Lab. 1990, 38, 342.
20. (c) Pinder, A.R. Nat. Prod. Rep. 1992, 9, 17.
21. (d) idem, Nat. Prod. Rep. ibid 1992, 9, 491.
22. (e) Plunkett, A.O. Nat. Prod. Rep. 1994, 11, 581.
23. (f) Harrison, T. Contemp. Org. Synth. 1995, 2, 209.
24. (g) Harrison, T. Contemp. Org. Synth. 1996, 3, 259.
25. Cook, G.R.; Beholz, L.G.; Stille, J.R. Tetrahedron Lett. 1994, 35, 1669, and literature cited therein.
26. Aguinaldo, A.M.; Reed, R.W. Phytochemistry 1990, 29, 2309.
27. Findlay, J.A. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1985; Vol. 26, pp 89-183.
28. For recent syntheses of pseudoconhydrine: (a) Stern, P.; Trska, P.; Ferles, M. Coll. Czech. Chem. Commun. 1974, 39, 2267.
29. (b) Enders, D.; Hassel, T.; Pieter, R.; Renger, B.; Seebach, D. Synthesis 1976, 548.
30. (c) Handling, K.E.; Burks, S.R. J. Org. Chem. 1984, 49, 40.
31. (d) Shono, T.; Matsumura, Y.; Onomura, O.; Sato, M. J. Org. Chem. 1988, 53, 4118.
32. (e) Plehiers, M.; Hootelé, C. Tetrahedron Lett. 1993, 34, 7569.
33. (f) Shono, T.; Matsumara, Y.; Onomura, O.; Kanazawa, T.; Habuka, M. Chem. Lett. 1994, 1101.
34. (g) Takahata, H.; Inose, K.; Momose, T. Heterocycles 1994, 38, 269.
35. (h) Oppolzer, W.; Bochet, C.G. Tetrahedron Lett. 1995, 36, 2959.
36. (i) Herdeis, C.; Held, W.A.; Kirfel, A.; Schwabenländer, F. Liebigs Ann. Chem. 1995, 1295.
37. (j) Sakagami, H.; Kamikubo, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1996, 1433.
38. (k) Moody, C.J.; Lightfoot, A.P.; Gallagher, P.T. J. Org. Chem. 1997, 62, 746.
39. (l) Fry, D.F.; Brown, M.; McDonald, J.C.; Dieter, R.K. Tetrahedron Lett. 1996, 37, 6227.
40. (m) Dockner, M.; Sasaki, N.A.; Riche, C.; Potier, P. Liebigs Ann./ Recueil 1997, 1267.
41. Herdeis, C. Synthesis 1986, 232.
42. Denney, D.B.; Ross, S.T. J. Org. Chem. 1962, 27, 998.
43. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602.
44. Huisgen, R. Helv. Chim. Acta 1967, 50, 2421.
45. Huisgen, R. J. Org. Chem. 1976, 41, 403.
46. Schultz, A.G.; Dittami, J.P.; Myong, S.O.; Sha, C.K. J. Am. Chem. Soc. 1983, 105, 3273.
47. Schultz, A.G.; McMahon, W.G. J. Org. Chem. 1984, 49, 1676.
48. Sha, C.K.; Ouyang, S.L.; Hsieh, D.Y.; Chang, R.C.; Chang, S.C. J. Org. Chem. 1986, 51, 1490.
49. Hassner, A.; Amarasekara, A.S.; Andisik, D. J. Org. Chem. 1988, 53, 27.
50. Natural product synthesis via 1,3 dipolar cycloaddition with azides: Hudlicky, T.; Frazier, J.O.; Kwart, L.D. Tetrahedron Lett. 1985, 26, 3523.
51. Buchanan, G.; Edgar, A.R.; Hewitt, B.D. J. Chem. Soc., Perkin Trans. 1 1987, 2371.
52. Bennett III, R.B.; Choi, J.-R.; Montgomery, W.D.; Cha, J.K. J. Am. Chem. Soc. 1989, 111, 2580.
53. Vasella, A.; Bernet, B.; Bulusu, Murty, A.R.C. Helv. Chim. Acta 1990, 73, 940.
54. Wild, R.; Schmidt, R.R. Liebigs Ann. Chem. 1995, 755.
55. Taber, D.F.; You, K.K. J. Am. Chem. Soc. 1995, 117, 5757.
56. Taber, D.F.; Rahimizadeh, M.; You, K.K. J. Org. Chem. 1995, 60, 529.
57. Pearson, W.H.; Schkeryantz, J.M. Tetrahdron 1996, 52, 3107.
58. For a review see also: Mulzer, J. Nachr. Chem. Lab. Tech. 1984, 32, 882 and 961.
59. Herdeis, C.; Schiffer, T. Tetrahdron 1996, 52, 14745.
60. For a review see also: Bunce, R.A. Tetrahedron 1995, 51, 13103.
61. Tietze, L.F.; Beifuss, U. Angew. Chem. 1993, 105, 137.
62. Ho, T.-L. Tandem Organic Reactions Wiley: New York, 1992.
63. Ziegler, F.E. Comprehensive Organic Synthesis Paquette, L.A., Ed.; Pergamon: Oxford, 1991; Vol. 5, Chapter 7.3.
64. Swern, D.; Mancuso, A.J. Synthesis 1981, 165 and literature cited therein.