Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reactions

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 5, 2001, Pages 523-528

  Harayama, Takashi ^a   Akamatsu, Hisashi ^a   Okamura, Kana ^a   Miyagoe, Taeko ^a   Akiyama, Toshihiko ^a   Abe, Hitoshi ^a   Takeuchi, Yasuo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COLUMN CHROMATOGRAPHY; HYDRIDES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; REDUCTION; SYNTHESIS (CHEMICAL);

COUPLING REACTIONS; CYCLIZATION REACTIONS;

AROMATIC HYDROCARBONS;

EID: 0035820163     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b008683p     Document Type: Article

References (41)

1. V. Simanek, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1985, vol. 26, p. 185.
2. J. Dostal and M. Potacek, Collect. Czech. Chem. Commun., 1990, 55, 2840.
3. M. Suffness and G.A. Cordell, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1985, vol. 25, p. 178.
4. S.P. MacKay, O. Meth-Cohn and R.D. Waigh, Adv. Heterocycl. Chem., 1997, 67, 345.
5. T. Ishikawa and H. Ishii, Heterocycles, 1999, 50, 627.
6. J.M. Herbert, J.M. Augereau, J. Gleye and J.P. Maffrand, Biochem. Biophys. Res. Commun., 1990, 172, 993.
7. S.-D. Fang, L.-K. Wang and S.M. Hecht, J. Org. Chem., 1993, 58, 5025.
8. T. Nakanishi and M. Suzuki, J. Nat. Prod., 1998, 61, 1263.
9. C. Vavreckova, I. Gawlik and K. Müller, Planta Med., 1996, 62, 397.
10. T. Schmeller, B. Latz-Brüning and M. Wink, Phytochemistry, 1997, 44, 257.
11. T. Nakanishi, M. Suzuki, A. Saimoto and T. Kabasawa, J. Nat. Prod., 1999, 62, 864; and references cited therein.
12. F. Fleury, A. Sukhanova, A. Ianoul, J. Devy, I. Kudelina, O. Duval, A.J.P. Alix, J.C. Jardillier and I. Nabiev, J. Biol. Chem., 2000, 275, 3501.
13. I. Ninomiya and T. Naito, Recent Dev. Chem. Nat. Carbon Compd., 1984, 10, 11.
14. Recent papers for synthesis of benzo[c]phenanthridine alkaloids: (a) T. Nakanishi and M. Suzuki, Org. Lett., 1999, 1, 985; and references cited therein.
15. (b) G.R. Geen, I.S. Mann, M.V. Mullane and A. McKillop, Tetrahedron, 1998, 54, 9875.
16. (c) T. Ishikawa, T. Saito and H. Ishii, Tetrahedron, 1995, 51, 8447.
17. (d) T. Minami, A. Nishimoto and M. Hanaoka, Tetrahedron Lett., 1995, 36, 9505.
18. (e) D. Seraphin, M.A. Lynch and O. Duval, Tetrahedron Lett., 1995, 36, 5731.
19. T. Harayama, T. Akiyama and K. Kawano, Chem. Pharm. Bull., 1996, 44, 1634.
20. T. Harayama and K. Shibaike, Heterocycles, 1998, 49, 191.
21. O. Hoshino, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1998, vol. 51, p. 323.
22. F. Viladomat, M. Selles, C. Codina and J. Bastida, Planta Med., 1997, 63, 583.
23. D.E. Ames and A. Opalko, Tetrahedron, 1984, 40, 1919.
24. D.H. Hey, G.H. Jones and M.J. Perkins, J. Chem. Soc. (C), 1971, 116.
25. W.R. Bowman, H. Heaney and B.M. Jordan, Tetrahedron, 1991, 47, 10119.
26. S.V. Kessar, R. Gopal and M. Singh, Tetrahedron, 1973, 29, 167.
27. (a) S.V. Kessar, D. Pal and M. Singh, Tetrahedron, 1973, 29, 177.
28. (b) S.V. Kessar, Y.P. Gupta, P. Balakrishnan, K.K. Sawal, T. Mohammad and M. Dutt, J. Org. Chem., 1988, 53, 1708.
29. (c) S. Prabhakar, A.M. Lobo and M.R. Tavares, J. Chem. Soc., Chem. Commun., 1978, 884.
30. (d) A.M. Rosa, A.M. Lobo, P.S. Branco, S. Prabhakar and A.M.D.L. Pereira, Tetrahedron, 1997, 53, 269.
31. (e) M.G. Banwell and C.J. Cowden, Aust. J. Chem., 1994, 47, 2235.
32. (f) H.Q. Yang and J.C. Cai, Youji Huaxue, 1997, 17, 234.
33. (g) H.W. Shao and J.C. Cai, Chin. Chem. Lett., 1997, 8, 493.
34. J.S. Swenton, K. Carpenter, Y. Chen, M.L. Kerns and G.W. Morrow, J. Org. Chem., 1993, 58, 3308.
35. Papers for synthesis: (a) A.S. Bailey and C.R. Worthing, J. Chem. Soc., 1956, 4535.
36. (b) V. Smula and R.H.F. Manske, Can. J. Chem., 1972, 50, 1544.
37. (c) J. Smidrkal, Collect. Czech. Chem. Commun., 1984, 49, 1412.
38. (d) G.R. Geen, G.I.S. Mann, M.V. Mullane and A. McKillop, Tetrahedron, 1998, 54, 9875.
39. S.F. Dyke and E.P. Tiley, Tetrahedron, 1975, 31, 561.
40. In synthetic studies on 12-methoxydihydrochelerythrine, a corresponding benzazepinone-type compound was obtained. See T. Harayama, T. Akiyama, H. Akamatsu, K. Kawano, H. Abe and Y. Takeuchi, Synthesis, in press.
41. K. Ohrai, K. Kondo, M. Sodeoka and M. Shibasaki, J. Am. Chem. Soc., 1994, 116, 11737.