Anodic fragmentation of catharanthine and coupling with vindoline. Formation of anhydrovinblastine

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 947-953

  Tabakovic, Ibro ^a   Gunic, Esmir ^a   Juranic, Ivan ^b  

^a University of Minnesota   (United States)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

ANHYDROVINBLASTINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030906102     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9621128     Document Type: Article

References (39)

1. Blasko, G.; Cordell, G. A. Isolation, Structure Elucidation and Biosynthesis of the Bisindole of Catharanthus. In The Alkaloids; Brossi, A., Suffness, M., Eds.; Academic Press, New York: 1990; Vol. 37, p 12.
2. Neus, N.; Neus, M. N. The Therapeutic Use of Bisindole Alkaloids from Catharanthus. In The Alkaloids; Brossi, A., Suffness, M., Eds.; Academic Press: New York, 1990; Vol. 37, p 232.
3. Kuehne, M. E.; Marko, I. Synthesis of Vinblastine Type Alkaloids. In The Alkaloids; Brossi, A., Suffness, M., Eds.; Academic Press: New York, 1990; Vol. 37, p 77.
4. (a) Raucher, S.; Bray, B. L. J. Org. Chem., 1985, 50, 3236.
5. (b) Szantay, C.; Bolcski, H.; Gasz-Baitz, E. Tetrahedron 1990, 46, 1711.
6. (c) Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y. J. Org. Chem. 1985, 50, 961.
7. Scott, A. I.; Gueritte, F.; Lee, S. L. J. Am. Chem. Soc. 1978, 100, 6253.
8. (a) Langlois, N.; Gueritte, F.; langlois, Y.; Potier, P. J. Am. Chem. Soc., 1976, 98, 7017.
9. (b) Kutney, J. P.; Hibino, T.; Jahngen, E.; Okutani, T.; Ratcliffe, A. H.; Treasurywaka, A. M.; Wunderly, S. Helv. Chim. Acta 1976, 59, 2858.
10. Kutney, J. P. Acc. Chem. Res. 1993, 26, 559 and the references therein.
11. Sundberg, R. J.; Gadamesetti, K. G.; Hunt, P. J. Tetrahedron 1992, 48, 277.
12. (a) Vukovic, J.; Goodbody, A. E.; Kutney, J. P.; Misawa, M. Tetrahedron 1988, 44, 325.
13. (b) Balazs, N.; Szantay, C., Jr.; Boleski, H.; Szantay, C. Tetrahedron Lett. 1993, 34, 4397.
14. (a) Kutney, J. P. Nat. Prod. Rep. 1990, 7, 87.
15. (b) Kuehne, M. E.; Matson, P. A.; Bornmann, W. G. J. Org. Chem. 1991, 56, 513.
16. (c) Magnus, P.; Stamford, A.; Ladlow, M. J. Am. Chem. Soc. 1990, 112, 8210.
17. (a) Sundberg, R. J.; Desos, P.; Gadamesatti, K. G.; Sabat, M. Tetrahedron Lett. 1991, 32, 3035.
18. (b) Sundberg, R. J.; Hunt, P. J.; Gadamesatti, K. G. J. Org. Chem., 1991, 56, 8210.
19. Gunic, E.; Tabakovic, I.; Gasic, M. J. J. Chem. Soc., Chem. Commun. 1993, 1496.
20. Tabakovic, I.; Gunic, E.; Gasic, M. J. J. Chem. Soc., Perkin Trans. 2 1996, 2741.
21. Nadjo, L.; Saveant, J.-M. J. Electroanal. Chem. 1973, 48, 113.
22. Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706.
23. Adams, R. N. Electrochemistry at Solid Electrodes; Marcel Dekker: New York, 1969.
24. Kuwana, T.; Bublitz, D. E.; Hoh, G. J. Am. Chem. Soc. 1960, 82, 5811.
25. Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 4790.
26. Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J. M.; M'Halla, F.; Saveant, J-M. J. Electroanal. Chem. 1980, 113, 19.
27. Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J. M.; M'Halla, F., Saveant, J.-M. J Am. Chem. Soc. 1980, 102, 3806.
28. Tabakovic, I.; Tabakovic, K. Tetrahedron Lett. 1996, 37, 3659.
29. Sundberg, R. J.; Bettiol, J. L.; Gadamesatti, K. G.; Marshala, M.; Kelsh, L. Bioorg. Med. Chem. Lett. 1994, 4, 1999.
30. (a) Nelsen, S. F.; Blackstock, S. C.; Steffek, D. J.; Cunkle, G. T.; Kurzweil, M. L. J. Am. Chem. Soc. 1988, 110, 6199.
31. (b) Nelsen, S. F.; Cuncle, G. T. J. Org. Chem. 1985, 50, 3701.
32. (c) Nelsen, S. F. J Org. Chem. 1984, 49, 1891.
33. (a) Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1285.
34. (b) Bischof, P. Croat. Chem. Acta 1980, 53, 51.
35. (c) Dewar, M. J. S.; Ford, G.; Rzepa, H. S.; Yamaguchi, Y. J. Mol. Struct. 1978, 43, 1325.
36. (d) Stewart, J. J. QCPE No. 455.
37. (e) Rzepa, H. S.; Wylie, W. A. J. Chem. Soc., Perkin Trans. 2 1991, 939.
38. (a) Gano, J. E.; Jacob, F. J.; Roesner, R. J. Comput. Chem. 1991, 12, 127.
39. (b) Smith, D. A.; Ulmer, C. W.; Gilbert, M. J. J. Comput. Chem. 1992, 13, 640.