A new approach to pyrrolophenanthridone alkaloids via intramolecular radical cyclization

Chemistry Letters

Volumn , Issue 2, 1998, Pages 155-156

  Tsuge, Otohiko ^a   Hatta, Taizo ^a   Tsuchiyama, Hiroshi ^a  

^a SOJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032377834     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.155     Document Type: Article

References (33)

1. S. F. Martin in "The Alkaloids"; A. Brossi Ed.; Academic Press: New York, 1987; Vol. 30, Charpter 3, pp 252-369; J. R. Lewis, Nat. Prod. Rep., 12, 339 (1995).
2. S. F. Martin in "The Alkaloids"; A. Brossi Ed.; Academic Press: New York, 1987; Vol. 30, Charpter 3, pp 252-369; J. R. Lewis, Nat. Prod. Rep., 12, 339 (1995).
3. S. C. Chattopadhyay, U. Chattopadhyay, P. P. Mathur, K. S. Saini, and S. Ghosal, Planta Med., 49, 252 (1983).
4. S. Ghosal, R. Lochan, A. Shutosh, Y Kumar, and R. S. Srivastava, Phytochemistry, 24, 1825 (1985).
5. a) R. H. Hutchings and A. I. Meyers, J. Org. Chem., 61, 1004 (1996);
6. b) C. Gonzalez, D. Perez, E. Guitian, and L. Castedo, J. Org. Chem., 61, 6318 (1995);
7. c) D. St. C. Black, P. A. Keller, and N. Kumar, Tetrahedron, 49, 151 (1993);
8. d) L. Castedo, E. Guitian, and D. Perez, Tetrahedron Lett., 33, 2407 (1992);
9. e) R. Grigg, A. Teasdale, and V. Sridharan, Tetrahedron Lett., 32, 3858 (1991);
10. f) L. Castedo, E. Guitian, and D. P. Meiras, Tetrahedron Lett., 31, 2331 (1990);
11. g) V. Snieckus and M. A. Siddiqui, Tetrahedron Lett., 31, 1523 (1990);
12. h) K. Hayakawa, T. Yasukouchi, and K. Kanematsu, Tetrahedron Lett., 28, 5895 (1987);
13. i) B. S. Joshi, H. K. Desai, and S. W. Pellether, J. Nat. Prod., 49, 445 (1986);
14. j) S. Ghosal, K. S. Saini, and A. W. Frahm, Phytochemistry 22, 2305 (1983).
15. a) D. P. Curran, T. L. Fevig, and C. P. Jasperse, Chem. Rev., 91, 1237 (1991);
16. b) D. P. Curran, Synthesis. 1988, 417 and 489;
17. c) W. P. Neuman, Synthesis. 1987, 665;
18. d) B. Giese, "Radicals in Organic Synthesis: Formation of Carbon Carbon Bonds", Oxford, 1986.
19. C. J. Moody and C. L. Norton, Tetrahedron Lett., 36, 9051 (1995) and references therein.
20. a) F. E. Ziegler and M. Belema, J. Org. Chem., 59, 7962 (1994);
21. b) F. E. Ziegler and P. G. Harran, J. Org. Chem., 58, 2768 (1993);
22. c) F. E. Ziegler and P. G. Harran, Tetraheron Lett., 34, 4505 (1993);
23. d) F. G. Ziegler and L. O. Jeronicic, J Org. Chem., 56, 3479 (1991).
24. S. Caddick, K. Aboutayab, and R. West, J. Chem, Soc., Chem. Commun., 1995, 1353; Synlett 1993, 231.
25. S. Caddick, K. Aboutayab, and R. West, J. Chem, Soc., Chem. Commun., 1995, 1353; Synlett 1993, 231.
26. A. P. Dobbs, K. Jones and K. T. Veal, Tetrahedron Lett., 36, 4857 (1995).
27. G. Bratoli, G. Palmieri, M. Bosco, and E. Dalpozzo, Tetrahedron Lett., 30, 2129 (1989).
28. All the new compounds gave satisfactory analytical and spectroscopic data.
29. 3) δ 101.62, 1002.27, 107.94, 110.73 (2), 116.63, 118.31, 122.55, 123.47 (2), 123.92, 128.35, 131.56, 148.46, 152.52, 158.06.
30. S. Ghosal, P. H. Rao, D. K. Jaiswal, Y. Kumar, and A. W. Frahm, Phytochemistry, 20, 2003 (1981).
31. Y. Kikugawa and M. Kashimura, Synthesis, 1982, 785.
32. The compound 9 (mp 111 °C) was obtained in 94% yield by the reaction of 3-methylindole with 2-bromobenzoyl chloride in the presence of NaH in dry THF.
33. +). Dehydrogenation of 10 (mp 124 °C) with 5% Pd-C in decalin (reflux, 20 h) gave 11 (mp174-175 °C) in 65% yield.