Asymmetric synthesis of both enantiomers of N-protected epibatidine via reductive heck-type hetarylation

Synlett

Volumn , Issue 6, 1999, Pages 804-806

  Namyslo, Jan Christoph ^a   Kaufmann, Dieter E ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Alkaloids; Asymmetric catalysis; C C coupling; Heterocycles; Palladium

Indexed keywords

EPIBATIDINE; NICOTINIC AGENT;

ALZHEIMER DISEASE; ANALGESIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MOLECULAR RECOGNITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032998103     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2719     Document Type: Article

References (49)

1. Part 3 of the Series "Chemistry in the Ambient Field of the Alkaloid Epibatidine". For Part 2 see Namyslo, J. C.; Kaufmann, D. E. Synlett 1999, 114.
2. a) Spande, T. F.; Garaffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem, Soc. 1992, 114, 3475.
3. b) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, jr., C.; Temesvari-Major, E.; Blasko, G. Tetrahedron Lett. 1994, 35, 3171.
4. a) Li, T.; Qian, C.; Eckman, J.; Huang, D. F.; Shen, T. Y. Bioorganic & Medicinal Chemistry Letters 1993, 3, 2759.
5. b) Qian, C.; Li, T.; Shen, T. Y.; Libertine-Garahan, L.; Eckman, J.; Biftu, T.; Ip, S. Eur. J. Pharmacol. 1993, 250, R13-R14.
6. c)Badio, B.; Daly, J. W. Mol. Pharmacol. 1994, 45, 563.
7. a) Maelicke, A. Nachr. Chem. Tech. Lab. 1995, 43, 444.
8. b) Lansbury, jr., P. T. Acc. Chem. Res. 1996, 29, 317.
9. Daly, J. W.; Tokuyama, T.; Fujiwara, T.; Highet, R. J.; Karle, I. L. J. Am. Chem. Soc. 1980, 102, 830.
10. a) Broka, C. A. Med. Chem. Res, 1994, 4, 449.
11. b) Dehmlow, E. V. J. Prakt. Chem. 1995, 337, 167.
12. c) Szántay, C.; Kardos-Balogh, Z.; Szántay, jr., C. The Alkaloids 1995, 46, 95-125.
13. d) Chen, Z.; Trudell, M. L. Chem. Rev, 1996, 96, 1179-1193.
14. e) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189-7191.
15. f) Giblin, G. M. P.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589-590.
16. g) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059.
17. h) Pandey, G.; Bagul, T. D.; Sahoo, A. K. J. Org. Chem. 1998, 63, 760.
18. a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683.
19. b) Campbell, J. A.; Rapoport, H. J. Org. Chem. 1996, 6t1, 6313.
20. c) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485.
21. d) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, jr., C.; Temesvari-Major, E.; Blasko, G. Tetrahedron 1996, 52, 11053.
22. e) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857.
23. f) Albertini, E., Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177.
24. g) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1023.
25. h) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397-8406.
26. i) Hall, A.; Baily, P. D.; Rees, D. C.; Wightman, R. H. Chem. Commun. 1998, 2251.
27. j) Clive, D. L, J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789,
28. Namyslo, J. C.; Kaufmann, D. E. Chem. Ber./Recueil 1997, 130, 1327.
29. Otten, A.; Namyslo, J. C.; Stoermer, M.; Kaufmann, D. E. Eur. J. Org. Chem. 1998, 1997.
30. Namyslo, J. C.;. Kaufmann, D. E. Synlett 1999, 114.
31. Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493.
32. N-(Methoxycarbonyl)-7-azabicydo[2.2.1]hept-2-ene (3) was obtained by the fluoride induced desilylation/detosylation procedure which we reported recently. See ref. [8].
33. 3S (261.60): calcd. C 27.55, H 1.16, N 5.35, S 12.26; found C 27.37, H 1.06, N 5.19, S 12.24.
34. 2: calc. 266.0822; found 266.0822.
35. a) Cortese, N. A.; Heck, R, F. J. Org. Chem. 1977, 42, 3491.
36. b) Chen, Q.-Y.; He, Y.-B.; Yang, Z.-Y. J. Chem. Soc., Chem. Common. 1986, 27, 1452.
37. c) Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1986, 27, 5541.
38. d) Cacchi, S.; Morera, E.; Ortar, G. Org. Synth. 1990, 138 and lit. cited therein.
39. Via bromination of 2-aminopyridine: Case, F. H. J. Am. Chem. Soc. 1946, 68, 2574.
40. Magidson, O.; Menschikoff, G. Ber. Dt. Chem. Ges. 1925, 58, 113.
41. a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
42. b) Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
43. c) Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1988, 67, 20.
44. d) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
45. a) Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
46. b) Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schocttel, G.; Zutter, U. Pure & Appl. Chem. 1996, 68, 131.
47. Laue, C.; Schroeder, G.; Arlt, D.; Grosser, R. (Bayer AG), EP 643.065, 1995 [Chem. Abstr. 1995, 123, 112406b].
48. Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927.
49. Namyslo, J. C. Ph.D. thesis, TU Clausthal 1998.