Stereoselective route towards 2,5-disubstituted piperidine alkaloids. Synthesis of (+)-pseudoconhydrine and (±)-epi-pseudoconhydrine

Tetrahedron

Volumn 56, Issue 15, 2000, Pages 2225-2230

  Löfstedt, Joakim ^a   Pettersson Fasth, Helena ^b   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

( ) epi pseudoconhydrine; (+) pseudoconhydrine

Indexed keywords

ALKALOID DERIVATIVE; PIPERIDINE DERIVATIVE; PSEUDOCONHYDRINE; UNCLASSIFIED DRUG;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0038584205     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01105-9     Document Type: Conference Paper

References (52)

1. (a) Strunzand, G. M.; Finlay, J. A. The alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1986; Vol. 26, p 89.
2. (b) Jones, T. H.; Blum, M. S.; Robertsson, H. G. J. Nat. Prod. 1990, 53, 429.
3. (a) Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977.
4. (b) Hasseberg, H.-A.; Gerlach, H. Liebigs. Ann. Chem. 1989, 255.
5. (a) Rice, W. Y.; Coke, J. L. J. Org. Chem. 1966, 31, 1010.
6. Highet R.J.J. Org. Chem. 1964, 29, 471.
7. (c) Highet, R. J.; Highet, P. F. J. Org. Chem. 1966, 31, 1275.
8. (d) Hill, R. K. Chemistry of the Alkaloids; Pelletier, S. W., New York, 1970, pp 385.
9. (e) Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914.
10. Ladenburg A., Adam G. Chem. Ber. 24:1891;1671.
11. (a) Marion, L.; Cockburn, W. F. J. Am. Chem. Soc. 1949, 49, 3402.
12. (b) Harding, K. E.; Burks, S. R. J. Org. Chem. 1984, 49, 40.
13. (c) Späth, E.; Kuffner, F.; Ensfeller, L. Chem. Ber. 1933, 66, 591.
14. (d) Brown, E.; Lavoue, J.; Dhal, R. Tetrahedron 1973, 29, 455.
15. (a) Tadano, K. I.; Iimura, Y.; Suami, T. J. Carbohydrate Chem. 1985, 4, 129.
16. (b) Takahata, H.; Inose, K.; Momose, T. Heterocycles 1994, 38, 269.
17. (c) Sakagami, H.; Kamikubo, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1996, 1433.
18. (d) Cossy, J.; Dumas, C.; Pardo, D. G. Synlett, 1997, 905.
19. (e) Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. J. Org. Chem. 1997, 62, 746.
20. (f) Oppolzer, W.; Bochet, C. G. Tetrahedron Lett. 1995, 36, 2959.
21. (g) Hirai, Y.; Shibuya, K.; Fukuda, Y.; Yokoyama, H.; Yamaguchi, S. Chem. Lett. 1997, 3, 221.
22. (h) Dockner, M.; Sasaki, N. A.; Riche, C.; Potier, P. Liebigs Ann., Recl. 1998, 6, 1267.
23. (i) Herdeis, C.; Schiffer, T. Synthesis 1997, 1405.
24. (j) Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783.
25. (a) Pettersson-Fasth, H.; Riesinger, S. W.; Bäckvall, J.-E. J. Org. Chem. 1995, 60, 6091.
26. (b) Riesinger, S. W.; Löfstedt, J.; Pettersson-Fasth, H.; Bäckvall, J.-E. Eur. J. Org. Chem. 1999, 3277.
27. (a) Byström, S. E.; Aslanian, R.; Bäckvall J. E. Tetrahedron Lett. 1985, 26, 1749.
28. (b) Kohrt, J. T.; Gu, J.-X.; Johnson, C. R. J. Org. Chem. 1998, 63, 5088.
29. For Pd(0)-catalyzed reactions of vinylepoxides with nucleophiles see: (a) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575.
30. (b) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969.
31. (c) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
32. (d) Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491.
33. (e) Tenaglia, A.; Waegell, B. Tetrahedron Lett. 1988, 29, 4851.
34. (f) Trost, B. M.; Romero, A. G. J. Org. Chem. 1986, 51, 2332.
35. (g) Tsuji, J. Pure & Appl. Chem. 1982, 54, 197.
36. (h) Trost, B. M.; Kou, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621.
37. (i) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421.
38. (j) Trost, B. M.; Bunt, R. C. Angew. Chem. 1996, 108, 70.
39. Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520.
40. Schink H.E., Pettersson H., Bäckvall J.E. J. Org. Chem. 56:1991;2769.
41. Bäckvall J.E., Andersson P.G., Stone G.B., Gogoll A. J. Org. Chem. 56:1991;2988.
42. Bäckvall J.E., Schink H.E., Renko Z.D. J. Org. Chem. 55:1990;826.
43. Yamazaki N., Kibayashi C. J. Am. Chem. Soc. 111:1989;1396.
44. Cunico R.F., Bedell L. J. Org. Chem. 45:1980;4797.
45. Trost B.M., Weber L., Strege P., Fullerton T.J., Dietsche T.J. J. Am. Chem. Soc. 100:1978;3426.
46. Schloss J.E., Hartman F.C. Bioorganic Chem. 9:1980;217.
47. 16
48. (b) McDonald, W. S.; Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 1997, 62, 1215.
49. Bouzide A., Sauvé G. Tetrahedron Lett. 34:1997;5945.
50. 2O significantly improved the yield of 18b.
51. (a) Katsuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373.
52. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, S.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.