Versatile approach to enantiopure 2,6-disubstituted piperidin-3-ol framework: Application to the total synthesis of (+)-deoxoprosopinine

Journal of Organic Chemistry

Volumn 69, Issue 14, 2004, Pages 4767-4773

  Wang, Qian ^a   Sasaki, N André ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ETHERS; OLEFINS; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR ALKYLATION; OLEFINATION;

AROMATIC COMPOUNDS;

2 TERT BUTYLDIPHENYL 3,4 O ISOPROPYLIDINE 2,3,4 TRIHYDROXYBUTYRALDEHYDE; 3 PHENYLSULFONYL 2 TERT BUTYLOXYCARBAMOYLPROPANOL BENZYL ETHER; BUTYRALDEHYDE; DEOXOPROSOPININE; ETHER DERIVATIVE; PIPERIDIN 3 OL DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ENANTIOMER; JULIA OLEFINATION; OLEFINATION; SYNTHESIS;

ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PIPERIDINES; STEREOISOMERISM;

EID: 3042704348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0496291     Document Type: Article

References (41)

1. Prosopis alkaloids from the leaves, stems, and roots of Prosopis africana: (a) Ratle, G.; Monseur, X.; Das, B. C.; Yassi, J.; Khuong-Huu, Q.; Goutarel, R. Bull. Soc. Chim. Fr. 1966, 2945-2947.
2. (b) Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442, 443-458.
3. For reviews that include piperidine alkaloids, see: (a) Ayer, W. A.; Habgood, T. E. In The Alkaloids; Manske, R. H., Ed.; Academic Press: London, 1968; Vol. 11, p 492.
4. (b) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183.
5. (c) Foder, G. B.; Colasanti, B. The Pyridine and Piperidine Alkaloids; Chemistry and Pharmacology. In Alkaloids: Chemical and Biological Perspectives: Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol. 3, pp 1-90.
6. (d) Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, pp 193-315 and references therein.
7. (e) Schneider, M. J. Pyridine and Piperidine Alkaloids: An Update. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, pp 155-299.
8. (f) Wang, C. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 585-621.
9. (g) Laschat, S.; Dickner, T.; Synthesis 2000, 1781-1813.
10. (h) Weintraub, P. M.; Sabd, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953-2989.
11. Analgesic, antibiotic and anaesthetic properties: (i) Bourrinet, P.; Quevauviller, A. C. R. Soc. Biol. 1968, 162, 1138-1140.
12. (j) Bourrinet, P.; Quevauviller, A. Ann. Pharm. Fr. 1968, 26, 787-796.
13. Sasaki, N. A.; Hashimoto, C.; Potier, P. Tetrahedron Lett. 1987, 28, 6069-6072.
14. (a) Wei, C. C.; De Bernardo, S.; Tengi, J. P.; Borgese, J.; Weigele, M. J. Org. Chem. 1985, 50, 3462-3467.
15. (b) Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K. J. Org. Chem. 1988, 53, 2598-2602.
16. (c) André, C.; Bolte, J.; Demuynck, C. Tetrahedron: Asymmetry 1998, 9, 1359-1367.
17. (a) Sakaitani, M.; Ohfune, Y. J. Org. Chem. 1990, 55, 870-876.
18. (b) Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543-5546.
19. (c) Sakaitani, M.; Kurokawa, N.; Ohfune, Y. Tetrahedron Lett. 1986, 27, 3753-3754.
20. (d) Hamada, Y.; Kato, S.; Shioiri, T. Tetrahedron Lett. 1985, 26, 3223-3226.
21. Sajiki, H. Tetrahedron Lett. 1995, 36, 3465-3468.
22. (a) Raub, M. F.; Cardellina, J. H., II; Choudhary, M. I.; Ni, C.-Z.; Clardy, J.; Alley, M. C. J. Am. Chem. Soc. 1991, 113, 3178-3180.
23. (b) Kong, F.; Faulkner, D. J. Tetrahedron Lett. 1991, 32, 3667-3668.
24. Previous synthesis of deoxoprosopinine (2): (a) Saitoh, Y.; Moriyama, Y.; Takahashi, T. Tetrahedron Lett. 1980, 21, 75-78.
25. (b) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488-492.
26. (c) Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39.
27. (d) Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475.
28. (e) Tadano, K.; Takao, K.; Nigawara, Y.; Nishino, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567.
29. (f) Takao, K.; Nigawara, Y.; Nishino, E.; Takagi, I.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704.
30. (g) Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526.
31. (h) Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1996, 793-802.
32. (i) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 7469-7470.
33. (j) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893.
34. (k) Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1098, 39, 3505-3508.
35. (l) Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796.
36. (m) Comins, D. L.; Sandelier, M. J.; Grillo, T. A. J. Org. Chem. 2001, 66, 6829-6832.
37. (n) For an asymmetric synthesis of (+) 2-epi-deoxoprosopinine, see: Enders, D.; Kirchhoff, J. H. Synthesis 2000, 2099-2105.
38. Previous synthesis of prosopinine (1): (a) Cook, J. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672 and references therein.
39. (b) Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777.
40. (c) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
41. (d) Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914-4919.