A new synthesis of all four stereoisomers of 2-(2,3- dihydroxypropyl)piperidine via iterative asymmetric dihydroxylation to cause enantiomeric enhancement. Application to asymmetric synthesis of naturally occurring piperidine-related alkaloids

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8594-8601

  Takahata, Hiroki ^a   Kubota, Minoru ^a   Ikota, Nobuo ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,3 DIHYDROXYPROPYL)PIPERIDINE; ALKALOID; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

EID: 0033550231     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991034w     Document Type: Article

References (42)

1. (a) Elbein, A. D.; Molyneux, R. In Alkaloids; Chemical and Biological perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1.
2. (b) O'Hagen, D. Nat. Prod. Rep. 1997, 14, 637.
3. (a) Sterino, C.; Stehle, N.; Park, Y. S.; Florio, S.; Beak, P. J. Org. Chem. 1999, 64, 1160.
4. (b) Pilli, R. A.; de Fatima Alves, C.; Bockelmann, M. A.; Mascarenhas, Y. P.; Nery J. G.; Vencato, I. Tetrahedron Lett. 1999, 40, 2891.
5. (c) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699.
6. (d) Reding, M. T.; Buchwald, S. L. J. Org. Chem. 1998, 63, 6344.
7. (e) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kuntz. H. Synthesis 1997, 1151.
8. (f) Munchhof, J. M.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084.
9. (a) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607.
10. (b) Takahata, H.; Inose, K.; Momose, T. Heterocycles 1994, 38, 269.
11. Takahata, H.; Kubota, M.; Takahashi, S.; Momose, T. Tetrahedron: Asymmetry 1996, 7, 3047.
12. For an excellent review, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
13. (a) Takahata, H.; Takahashi, S.; Kouno S.; Momose, T. J. Org. Chem. 1998, 63, 2224.
14. (b) Takahata, H.; Kouno S.; Momose, T. Tetrahedron: Asymmetry 1995, 6, 1085.
15. Baba, S. E.; Sartor, K.; Poulin, J.-C.; Kagan, H. B. Bull. Soc. Chim. Fr. 1994, 131, 525.
16. A part of this work has been published as a preliminary communication. Takahata, H.; Kubota, M.; Momose, T. Tetrahedron Lett. 1997, 38, 3451.
17. Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
18. Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515.
19. (a) Micel, K.-H.; Sandberg, F.; Haglid, F.; Norin, T. Acta Pharm. Suec. 1967, 4, 97.
20. (b) Micel, K.-H.; Sandberg, F.; Haglid, F.; Norin, T.; Chan, R. P. K.; Craig, J. C. Acta Chem. Scand. 1969, 23, 3479.
21. (a) Marion, L.; Chaput, M. Can. J. Res. 1949, 27, 215.
22. (b) Beyerman, H. C.; Bordes, B. S. L.; Maat, L.; Warnaar, F. M. Recl. Trav. Chim. Pays-Bas 1972, 91, 1441.
23. (c) Kim, J. H.; T'Hart, H.; Stevens, J. F. Phytochemistry 1996, 41, 1319.
24. Schöpf, C.; Kauffmann, T. Justus Liebigs Ann. Chem. 1957, 608, 88.
25. Schneider, M. J.; Brendze, S.; Montali, J. A. Phytochemistry 1995, 39, 1387.
26. (a) Beyerman, H. C.; Maat, L.; Van Veen, A.; Zweistra, A.; von Philipsborn, W. Recl. Trav. Chim. Pays-Bas 1965, 84, 1367.
27. (b) Murahashi, S. Imada, Y.; Kohno, M.; Kawakami, T. Synlett 1993, 395.
28. (c) Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1997, 8, 109.
29. (d) Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. Synlett 1997, 22.
30. Recently, the same correction of the absolute configuration of (+)-8-ethylnorlobelol-I was proposed. Mill, S.; Durant, A.; Hootelé, C. Liebigs Ann. 1996, 2083.
31. (a) Schöpf, C.; Gams, E.; Koppernock, F.; Rausch, R. Wallbe, R. Liebigs Ann. Chem. 1970, 732, 181.
32. (b) Stevens, J. F.; T'Hart, H.; Hendriks, H.; Malingré, T. M. Phytochemistry 1992, 31, 3917.
33. The absolute configurations of both allosedridine (12) and N-methylsedridine (13) remain unknown.
34. (a) Merlin, P.; Breakman, J.-C.; Daloze, D.; Pasteels, J.-M. J. Chem. Ecol. 1988, 14, 517.
35. (b) Breakman, J.-C.; Daloze, D.; Pasteels, J.-M.; Vanhecke, P.; Declercq, J.-P.; Sinnwell, V.; Franke, W. Z. Naturforsch. 1987, 42C, 627.
36. Racemic form: (a) Merlin, P.; Breakman, J.-C.; Daloze, D. Tetrahedron Lett. 1988, 29, 1691. (b) Jones, T. H. Tetrahedron Lett. 1990, 31, 1535. (c) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543. (d) Barluenga, J. Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 3699. Chiral form: (e) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.- P. J. Org. Chem. 1996, 61, 4949. (f) Marcours, P.; Breakman, J.-C.; Daloze, D. Tetrahedron 1995, 51, 1415.
37. Racemic form: (a) Merlin, P.; Breakman, J.-C.; Daloze, D. Tetrahedron Lett. 1988, 29, 1691. (b) Jones, T. H. Tetrahedron Lett. 1990, 31, 1535. (c) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543. (d) Barluenga, J. Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 3699. Chiral form: (e) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.- P. J. Org. Chem. 1996, 61, 4949. (f) Marcours, P.; Breakman, J.-C.; Daloze, D. Tetrahedron 1995, 51, 1415.
38. Racemic form: (a) Merlin, P.; Breakman, J.-C.; Daloze, D. Tetrahedron Lett. 1988, 29, 1691. (b) Jones, T. H. Tetrahedron Lett. 1990, 31, 1535. (c) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543. (d) Barluenga, J. Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 3699. Chiral form: (e) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.- P. J. Org. Chem. 1996, 61, 4949. (f) Marcours, P.; Breakman, J.-C.; Daloze, D. Tetrahedron 1995, 51, 1415.
39. Racemic form: (a) Merlin, P.; Breakman, J.-C.; Daloze, D. Tetrahedron Lett. 1988, 29, 1691. (b) Jones, T. H. Tetrahedron Lett. 1990, 31, 1535. (c) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543. (d) Barluenga, J. Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 3699. Chiral form: (e) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.- P. J. Org. Chem. 1996, 61, 4949. (f) Marcours, P.; Breakman, J.-C.; Daloze, D. Tetrahedron 1995, 51, 1415.
40. Racemic form: (a) Merlin, P.; Breakman, J.-C.; Daloze, D. Tetrahedron Lett. 1988, 29, 1691. (b) Jones, T. H. Tetrahedron Lett. 1990, 31, 1535. (c) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543. (d) Barluenga, J. Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 3699. Chiral form: (e) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 4949. (f) Marcours, P.; Breakman, J.-C.; Daloze, D. Tetrahedron 1995, 51, 1415.
41. Racemic form: (a) Merlin, P.; Breakman, J.-C.; Daloze, D. Tetrahedron Lett. 1988, 29, 1691. (b) Jones, T. H. Tetrahedron Lett. 1990, 31, 1535. (c) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543. (d) Barluenga, J. Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 3699. Chiral form: (e) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.- P. J. Org. Chem. 1996, 61, 4949. (f) Marcours, P.; Breakman, J.-C.; Daloze, D. Tetrahedron 1995, 51, 1415.
42. Under an atmosphere of hydrogen, only the hydrogenolysis of N-Cbz proceeded to give no cyclized product. Cf. Scovill, J. P.; Burckhalter, J. H. J. Heterocycl. Chem. 1980, 17, 23.