Palladium(II)-catalyzed 1,4-oxidation of 2-aryl-1,3-cyclohexadienes. Application to the synthesis of (±)-epibatidine and analogues

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 836-842

  Palmgren, Andreas ^a,b   Larsson, Anna L E ^a   Bäckvall, Jan E ^a,b   Helquist, Paul ^c  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

^c UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOHEXENE DERIVATIVE; EPIBATIDINE; PALLADIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033525109     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981668n     Document Type: Article

References (52)

1. (a) Bäckvall, J. E. Palladium-Catalyzed 1,4-Additions to Conjugated Dienes. Review in Metal-catalyzed Cross Coupling Reactions; Stang, P., Diederich, F., Eds.; VCH: Weinham, 1998; pp 339-382.
2. (b) Bäckvall, J. E. In The Chemistry of Functional Groups: Polyenes and Dienes; Patai S., Rappoport, Z., Eds.; Wiley: New York, 1996; pp 653-682.
3. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12 (Vol. Ed. Hegedus, L. S.), p 797.
4. (d) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 1995.
5. (a) Bäckvall, J. E.; Nyström, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676.
6. (b) Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
7. (a) Andersson, P. G.; Bäckvall, J. E. In Advances in Natural Product Synthesis; Pearson, W., Ed.; JAI Press: Greenwich, CT, 1996; pp 179-215.
8. (b) Tanner, D.; Sellén, M.; Bäckvall, J. E. J. Org. Chem. 1989, 54, 3374.
9. (c) Schink H. E.; Pettersson, H.; Bäckvall, J. E. J. Org. Chem. 1991, 56, 2769.
10. (d) Bäckvall, J. E.; Renko, Z. D.; Byström, S. E. Tetrahedron Lett. 1987, 28, 4199.
11. Some selected examples where this methodology has been used by others in natural product synthesis, see: (a) Pearson, A. J.; Lai, Y. S.; Lu, W.; Pinkerton, A. A. J. Org. Chem. 1989, 54, 3882. (b) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256. (c) Johnson, C. R.; Golebiowski, A.; Steensma, D. H.; Scialdone, M. A. J. Org. Chem. 1993, 58, 7185. (d) Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
12. Some selected examples where this methodology has been used by others in natural product synthesis, see: (a) Pearson, A. J.; Lai, Y. S.; Lu, W.; Pinkerton, A. A. J. Org. Chem. 1989, 54, 3882. (b) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256. (c) Johnson, C. R.; Golebiowski, A.; Steensma, D. H.; Scialdone, M. A. J. Org. Chem. 1993, 58, 7185. (d) Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
13. Some selected examples where this methodology has been used by others in natural product synthesis, see: (a) Pearson, A. J.; Lai, Y. S.; Lu, W.; Pinkerton, A. A. J. Org. Chem. 1989, 54, 3882. (b) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256. (c) Johnson, C. R.; Golebiowski, A.; Steensma, D. H.; Scialdone, M. A. J. Org. Chem. 1993, 58, 7185. (d) Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
14. Some selected examples where this methodology has been used by others in natural product synthesis, see: (a) Pearson, A. J.; Lai, Y. S.; Lu, W.; Pinkerton, A. A. J. Org. Chem. 1989, 54, 3882. (b) Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256. (c) Johnson, C. R.; Golebiowski, A.; Steensma, D. H.; Scialdone, M. A. J. Org. Chem. 1993, 58, 7185. (d) Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
15. Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475.
16. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
17. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
18. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
19. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
20. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
21. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
22. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
23. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
24. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
25. Broka, C. Med. Chem. Res. 1994, 4, 449; this review describes nine total syntheses until September 1994. For later work not covered by this review, see ref 7 and (b) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (c) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (d) Aben, R. W. M.; Keijsers, J.; Hams, B.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 1299. (e) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (f) Albertini, E.; Barco, A.; Beretti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Gonzales, J.; Koontz, J. I.; Hodges, L. M.; Nilsson, K. R.; Neely, L. K.; Myers, W. H.; Sabat, M.; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. (i) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (j) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
26. (a) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600.
27. (b) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463.
28. (c) Malpass, J. R.; Hemmings, D. A.; Wallis, A. L. Tetrahedron Lett. 1996, 37, 3911.
29. (d) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485.
30. (e) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053.
31. (f) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189.
32. (g) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, P.; Zanirato, V. Tetrahedron Lett. 1997, 38, 681.
33. (h) Zhang, C.; Gyermek, L.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 5619.
34. (i) Giblin, G. M. P.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
35. (j) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857.
36. (k) Pandey, G.; Bagul, T. D.; Sahoo, A. K. J. Org. Chem. 1998, 63, 760.
37. (l) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1023.
38. (m) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059.
39. (n) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
40. (o) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. Tetrahedron Lett. 1998, 39, 4513.
41. Karlström, S.; Rönn, M.; Thorarensen, A.; Bäckvall, J. E. J. Org. Chem. 1998, 63, 2517.
42. Bäckvall, J. E.; Granberg, K. L.; Hopkins, R. B. Acta Chem. Scand. 1990, 44, 492.
43. Heathcock, C. H.; Blumenkopf, T. A.; Smith, K. M. J. Org. Chem. 1989, 54, 1548.
44. (a) Thompson, H. W.; McPherson, E.; Lences, B. L. J. Org. Chem. 1976, 41, 2903.
45. (b) Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 106, 1072.
46. (c) Evans, D. A.; Morrissey, M. M. J. Am. Chem. Soc. 1984, 706, 3866.
47. (d) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986, 51, 2655.
48. (a) Okabe, K.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 1432.
49. (b) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417.
50. Bottini, F.; Di Grazia, M.; Finocchiaro, P.; Fronczek, F. R.; Mamo, A.; Pappalardo, S. J. Org. Chem. 1988, 53, 3521.
51. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1990.
52. Testaferri, L.; Tiecco, M.; Tingoli, M.; Bartoli, D.; Massoli, A. Tetrahedron 1985, 41, 1373.