Transition metal complexes in organic synthesis, part 73. Synthetic routes to naturally occurring furocarbazoles

Heterocycles

Volumn 63, Issue 10, 2004, Pages 2393-2407

  Fröhner, Wolfgang ^a   Krahl, Micha P ^a   Reddy, Kethiri R ^a   Knölker, Hans Joachim ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBAZOLE DERIVATIVE; EUSTIFOLINE D; FUROCARBAZOLE; FUROCLAUSINE A; FUROCLAUSINE B; FUROSTIFOLINE; FURO[3,2 A]CARBAZOLE ALKALOID; INDOLE DERIVATIVE; IRON COMPLEX; PLANT EXTRACT; UNCLASSIFIED DRUG;

CHINESE MEDICINE; COMPLEX FORMATION; CYCLIZATION; DRUG ISOLATION; DRUG SYNTHESIS; NONHUMAN; PHYTOCHEMISTRY; REVIEW; STEREOCHEMISTRY; TRADITIONAL MEDICINE;

EID: 7044235100     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/rev-04-585     Document Type: Review

References (68)

1. Part 72: H.-J. Knölker, E. Baum, and M. Kosub, Synlett, 2004, in print.
2. R. S. Kapil, The Alkaloids, ed. by R. H. F. Manske, Academic Press, New York, 1971, Vol. 13, p. 273.
3. D. P. Chakraborty, Progress in the Chemistry of Organic Natural Products, ed. by W. Herz and H. Grisebach, Springer, Wien, 1977, Vol. 34, p. 299.
4. H. P. Husson, The Alkaloids, ed. by A. Brossi, Academic Press, New York, 1985, Vol. 26, p. 1.
5. P. Bhattacharyya and D. P. Chakraborty, Progress in the Chemistry of Organic Natural Products, ed. by W. Herz, H. Grisebach, G. W. Kirby, and C. Tamm, Springer, Wien, 1987, Vol. 52, p. 159.
6. D. P. Chakraborty and S. Roy, Progress in the Chemistry of Organic Natural Products, ed. by W. Herz, H. Grisebach, G. W. Kirby, W. Steglich, and C. Tamm, Springer, Wien, 1991, Vol. 57, p. 71.
7. D. P. Chakraborty, The Alkaloids, ed. by G. A. Cordell, Academic Press, New York, 1993, Vol. 44, p. 257.
8. H.-J. Knölker and K. R. Reddy, Chem. Rev., 2002, 102, 4303.
9. D. P. Chakraborty and S. Roy, Progress in the Chemistry of Organic Natural Products, ed. by W. Herz, H. Grisebach, G. W. Kirby, W. Steglich, and C. Tamm, Springer, Wien, 2003, Vol. 85, p. 125.
10. H.-J. Knölker, Topics in Current Chemistry: Natural Product Synthesis II - Targets, Methods, Concepts, ed. by J. H. Mulzer, Springer, Heidelberg, 2004, Vol. 244, in print.
11. U. Pindur, Chimia, 1990, 44, 406.
12. J. Bergman and B. Pelcman, Pure Appl. Chem., 1990, 62, 1967.
13. H.-J. Knölker, Synlett, 1992, 371.
14. T. Kawasaki and M. Sakamoto, J. Indian Chem. Soc., 1994, 71, 443.
15. C. J. Moody, Synlett, 1994, 681.
16. U. Pindur, Advances in Nitrogen Heterocycles, ed. by C. J. Moody, JAI Press, Greenwich (CT), 1995, Vol. 1, p. 121.
17. H.-J. Knölker, Advances in Nitrogen Heterocycles, ed. by C. J. Moody, JAI Press, Greenwich (CT), 1995, Vol. 1, p. 173.
18. S. Hibino and E. Sugino, Advances in Nitrogen Heterocycles, ed. by C. J. Moody, JAI Press, Greenwich (CT), 1995, Vol. 1, p. 205.
19. H.-J. Knölker, Chem. Soc. Rev., 1999, 28, 151.
20. H.-J. Knölker, Curr. Org. Synthesis, 2004, 1, no. 4.
21. V. K. Kansal and P. Poitier, Tetrahedron, 1986, 42, 2389.
22. G. W. Gribble, The Alkaloids, ed. by A. Brossi, Academic Press, New York, 1990, Vol. 39, p. 239.
23. G. W. Gribble, Synlett, 1991, 289.
24. M. Gill and W. Steglich, Progress in the Chemistry of Organic Natural Products, ed. by W. Herz, H. Grisebach, G. W. Kirby, and C. Tamm, Springer, Wien, 1987, Vol. 51, p. 216.
25. G. W. Gribble and S. J. Berthel, Studies in Natural Products Chemistry, ed. by Atta-ur-Rahman, Elsevier, Amsterdam, 1993, Vol. 12, p. 365.
26. M. Prudhomme, Curr. Pharm. Des., 1997, 3, 265.
27. U. Pindur, Y.-S. Kim, and F. Mehrabani, Curr. Med. Chem., 1999, 6, 29.
28. (a) M. Chakrabarty and S. Khasnobis, J. Indian Chem. Soc., 1997, 74, 917.
29. (b) M. Chakrabarty, N. Ghosh, and Y. Harigaya, Heterocycles, 2004, 62, 779.
30. (a) G. H. Kirsch, Curr. Org. Chem., 2001, 5, 507.
31. (b) I. C. F. R. Ferreira, M.-J. R. P. Queiroz, and G. Kirsch, Tetrahedron, 2002, 58, 7943.
32. (c) I. C. F. R. Ferreira, M.-J. R. P. Queiroz, and G. Kirsch, Tetrahedron, 2003, 59, 3737.
33. (d) I. C. F. R. Ferreira, M.-J. R. P. Queiroz, and G. Kirsch, Tetrahedron Lett., 2003, 44, 4327.
34. (a) N. Haider, J. Heterocycl. Chem., 2002, 39, 511.
35. (b) N. Haider and E. Sotelo, Chem. Pharm. Bull., 2002, 50, 1479.
36. C. Ito and H. Furukawa, Chem. Pharm. Bull., 1990, 38, 1548.
37. T.-S. Wu, S.-C. Huang, and P.-L. Wu, Heterocycles, 1997, 45, 969.
38. (a) A. Sato, T. Morishita, T. Shiraki, S. Yoshioka, H. Horikoshi, H. Kuwano, H. Hanzawa, and T. Hata, J. Org. Chem., 1993, 58, 7632.
39. (b) K. Warabi, S. Matsunaga, R. W. M. van Soest, and N. Fusetani, J. Org. Chem., 2003, 68, 2765.
40. R. G. S. Berlinck, R. Britton, E. Piers, L. Lim, M. Roberge, R. M. da Rocha, and R. J. Andersen, J. Org. Chem., 1998, 63, 9850.
41. T.-S. Wu, M.-L. Wang, and P.-L. Wu, Phytochemistry, 1996, 43, 785.
42. E. Y. Murugova, O. B. Romanova, A. S. Sokolova, I. S. Nikolaeva, T. V. Pushkina, A. N. Fomina, and V. G. Granik, Khim. Farm. Zh., 1990, 24, 44.
43. (a) D. Joseph, L. Martarello, and G. Kirsch, J. Chem. Res. S, 1995, 350; M 2001.
44. (b) D. Joseph, L. Martarello, and G. Kirsch, J. Chem. Res. S, 1995, 448; M 2557.
45. (a) G. Jones and W. H. McKinley, Tetrahedron Lett., 1977, 2457.
46. (b) G. Jones and W. H. McKinley, J. Chem. Soc., Perkin Trans. 1, 1979, 599.
47. E. M. Beccalli, A. Marchesini, and T. Pilati, Tetrahedron, 1993, 49, 4741.
48. A. R. Katritzky and L. Xie, J. Org. Chem., 1995, 60, 3707.
49. H.-J. Knölker and W. Fröhner, Tetrahedron Lett., 1996, 37, 9183.
50. H.-J. Knölker and W. Fröhner, Synthesis, 2000, 2131.
51. H.-J. Knölker, E. Baum, P. Gonser, G. Rohde, and H. Röttele, Organometallics, 1998, 17, 3916.
52. H.-J. Knölker, Chem. Rev., 2000, 100, 2941.
53. E. O. Fischer and R. D. Fischer, Angew. Chem., 1960, 72, 919.
54. H.-J. Knölker, G. Baum, N. Foitzik, H. Goesmann, P. Gonser, P. G. Jones, and H. Röttele, Eur. J. Inorg. Chem., 1998, 993.
55. E. M. Beccalli, F. Clerici, and A. Marchesini, Tetrahedron, 1998, 54, 11675.
56. H. Hagiwara, T. Choshi, H. Fujimoto, E. Sugino, and S. Hibino, Chem. Pharm. Bull., 1998, 46, 1948.
57. H. Hagiwara, T. Choshi, J. Nobuhiro, H. Fujimoto, and S. Hibino, Chem. Pharm. Bull., 2001, 49, 881.
58. (a) K. E. Schulte, J. Reisch, and U. Stoess, Angew. Chem., 1965, 77, 1141; Angew. Chem., Int. Ed. Engl., 1965, 4, 1081.
59. (a) K. E. Schulte, J. Reisch, and U. Stoess, Angew. Chem., 1965, 77, 1141; Angew. Chem., Int. Ed. Engl., 1965, 4, 1081.
60. (b) J. P. Konopelski, J. M. Hottenroth, H. Monzó Oltra, E. A. Véliz, and Z.-C. Yang, Synlett, 1996, 609.
61. T. Soós, G. Timári, and G. Hajós, Tetrahedron Lett., 1999, 40, 8607.
62. J. I. G. Cadogan, Synthesis, 1969, 11.
63. G. A. Olah, L. Ohannesian, and M. Arvanaghi, Synthesis, 1986, 868.
64. A. Yasuhara, N. Suzuki, and T. Sakamoto, Chem. Pharm. Bull., 2002, 50, 143.
65. J. Koyanagi, K. Yamamoto, K. Nakayama, and A. Tanaka, J. Heterocycl. Chem., 1995, 32, 1289.
66. H.-J. Knölker and M. P. Krahl, Synlett, 2004, 528.
67. H.-J. Knölker, B. Ahrens, P. Gonser, M. Heininger, and P. G. Jones, Tetrahedron, 2000, 56, 2259.
68. A. J. Birch, P. E. Cross, J. Lewis, D. A. White, and S. B. Wild, J. Chem. Soc. A, 1968, 332.