Synthesis and oxidative fragmentation of catharanthine analogs. Comparison to the fragmentation - Coupling of catharanthine and vindoline

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6259-6292

  Sundberg, Richard J ^a   Hong, Jian ^a   Smith, Stanton Q ^a   Sabat, Michal ^a   Tabakovic, Ibro ^b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,1 CATHARANTHINE; 3,2 CATHARANTHINE; ALKALOID; ALKALOID DERIVATIVE; CATHARANTHINE; DEETHYL(2,1) CATHARANTHINE; DEETHYL(3,2) CATHARANTHINE; UNCLASSIFIED DRUG; VINCA ALKALOID; VINDOLINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; OXIDATION REDUCTION POTENTIAL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

VINCA;

EID: 0032482284     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00289-0     Document Type: Article

References (62)

1. (1) Noble, R. L. Biochem. Cell Biol., 1990, 68, 1344-1351; Gerzon, K. in Anticancer Agents Based on Natural Product Models, Cassady, J. M.; Douros, J. D., editors Academic Press, New York, 1980.
2. (1) Noble, R. L. Biochem. Cell Biol., 1990, 68, 1344-1351; Gerzon, K. in Anticancer Agents Based on Natural Product Models, Cassady, J. M.; Douros, J. D., editors Academic Press, New York, 1980.
3. (2) Lu, M. C. in Foye, W. D. editor, Cancer Chemotherapeutic Agents, Am. Chem. Soc., 1995, pp 350-353.
4. (3) Johnson, S. A.; Harper, P.; Hortobogyi, G. N.; Pouillart, P., Cancer Treat. Rev., 1996, 22, 127-142.
5. (4) Reviewed by Pearce, H. L., The Alkaloids, 1990, 37, 145-204.
6. (5) Reviewed by Potier, P.; J. Nat. Prod., 1980, 43, 72-85. Kutney, J. P., Nat. Prod. Rept., 1990, 85-103; Kutney, J. P., Synlett, 1991, 11-19; Kutney, J. P., Acc. Chem. Res., 1993, 26, 559-566.
7. (5) Reviewed by Potier, P.; J. Nat. Prod., 1980, 43, 72-85. Kutney, J. P., Nat. Prod. Rept., 1990, 85-103; Kutney, J. P., Synlett, 1991, 11-19; Kutney, J. P., Acc. Chem. Res., 1993, 26, 559-566.
8. (5) Reviewed by Potier, P.; J. Nat. Prod., 1980, 43, 72-85. Kutney, J. P., Nat. Prod. Rept., 1990, 85-103; Kutney, J. P., Synlett, 1991, 11-19; Kutney, J. P., Acc. Chem. Res., 1993, 26, 559-566.
9. (5) Reviewed by Potier, P.; J. Nat. Prod., 1980, 43, 72-85. Kutney, J. P., Nat. Prod. Rept., 1990, 85-103; Kutney, J. P., Synlett, 1991, 11-19; Kutney, J. P., Acc. Chem. Res., 1993, 26, 559-566.
10. (6) Reviewed by Kuehne, M. E.; Marko, I., The Alkaloids, 1990, 37, 77-131; Magnus, P.; Mendoza, J. S.; Stamford, A.; Ladlow, M.; Willis, P., J. Am. Chem. Soc., 1992, 114, 10232-10245.
11. (6) Reviewed by Kuehne, M. E.; Marko, I., The Alkaloids, 1990, 37, 77-131; Magnus, P.; Mendoza, J. S.; Stamford, A.; Ladlow, M.; Willis, P., J. Am. Chem. Soc., 1992, 114, 10232-10245.
12. (7) (a) Sundberg, R. J.; Bloom, J. D. J. Org. Chem. 1981, 46, 4836-4842;
13. (b) Sundberg, R. J.; Cherney, R. J. J. Org. Chem. 1990, 55, 6028-6037;
14. (c) Sundberg, R. J.; Amat, M.; Fernando, A. M. J. Org. Chem. 1987, 52, 3151-3159;
15. (d) Sundberg, R. J.; Gadamasetti, K. G. Tetrahedron, 1991, 47, 5673-5680.
16. (8) Sundberg, R. J.; Bloom, J. D. J. Org. Chem. 1980, 45, 3382-3387.
17. (9) Hamada, T.; Nishida, A.; Yonemitsu, O. J. Am. Chem. Soc. 1986, 108, 140-145.
18. (10) Szantay, C.; Keve, T.; Bölcskei, H.; Acs, T. Tetrahedron Lett. 1983, 24, 5539-5542; Szantay, C.; Bölcskei, H.; Gacs-Baitz, E. Tetrahedron 1990, 46, 1711-1732.
19. (10) Szantay, C.; Keve, T.; Bölcskei, H.; Acs, T. Tetrahedron Lett. 1983, 24, 5539-5542; Szantay, C.; Bölcskei, H.; Gacs-Baitz, E. Tetrahedron 1990, 46, 1711-1732.
20. (11) Szantay, C.; Bölcskei, H.; Gacs-Baitz, E.; Keve, T. Tetrahedron 1990, 46, 1687-1710.
21. (12) Biswas, K. M.; Jackson, A. H. Tetrahedron 1968, 24, 1145-1162.
22. (13) Methyl 2-(1-phenysulfonyl)indole-3-propenoate was prepared by low temperature addition of 3-lithio-1-phenylsulfonylindole to methyl pyruvate, followed by dehydration with Burgess reagent.
23. (14) Raucher, S.; Bray, G. L. J. Org. Chem. 1985, 50, 3237-3239; Raucher, S.; Bray, B. L.; Lawrence, R. F. J. Am. Chem. Soc. 1987, 109, 442-446.
24. (14) Raucher, S.; Bray, G. L. J. Org. Chem. 1985, 50, 3237-3239; Raucher, S.; Bray, B. L.; Lawrence, R. F. J. Am. Chem. Soc. 1987, 109, 442-446.
25. (15) (a) Langlois, N.; Gueritte, F.; Langlois, Y.; Potier, P., J. Am. Chem. Soc., 1976, 98, 7017-7024;
26. (b) Kutney, J. P.; Choi, L. S. L.; Nakano, J.; Tsukamoto, H.; McHugh, M.; Boulet, C. A., Heterocycles, 1988, 27, 1845-1853.
27. (16) (a) Goodbody, A. E.; Endo, T.; Vukovic, J.; Kutney, J. P.; Choi, L. S.; Misawa, M., Planta Medica, 1988, 54, 210-214;
28. (b) Kutney, J. P.; Vukovic, J.; Goodbody, A. E.; Misawa, M., Tetrahedron, 1988, 44, 325-331;
29. (c) Tan, M.; Sakamoto, N.; Hata, E.; Ishitoku, T.; Kihara, N., Eur. Pat. Appl Ep 354 778, 1990; Chem. Abstr., 1990, 113, 66635;
30. (c) Tan, M.; Sakamoto, N.; Hata, E.; Ishitoku, T.; Kihara, N., Eur. Pat. Appl Ep 354 778, 1990; Chem. Abstr., 1990, 113, 66635;
31. (d) Szantay, C., Jr.; Balazs, J.; Bolcskei, J.; Szantay, C., Tetrahedron, 1991, 47, 1265-1274;
32. (e) Sakamoto, N.; Tan, H.; Hata, E.; Kihara, N.; Jpn. Kokai Tokkyo Koho JP 0341,081; Chem. Abstr., 1991, 115, 50074.
33. (17) Photochemical: Huhtikangas, A.; Pennanen, S.; Lounasmaa, M.; 1989, PCT Int. WO89 12 056 Chem. Abstr., 1990, 112, 198,880; Pennanen, S.; Huhtikangas, A., Photochem. Photobiol., 1990, 51, 515-518; Hirata, K.; Duangteraprecha, S.; Morihara, E.; Honda, M.; Akagi, T.; Nakae, M.; Katayama, M.; Miyamoto, K., Biotech. Lett., 1997, 79, 53-57; Duangteraprecha, S.; Hirato, K.; Morihara, E.; Nakae, M.; Katayama, H.; Honda, M.; Miyamoto, K.; J. Ferment. Bioeng., 1997, 83, 227.
34. (17) Photochemical: Huhtikangas, A.; Pennanen, S.; Lounasmaa, M.; 1989, PCT Int. WO89 12 056 Chem. Abstr., 1990, 112, 198,880; Pennanen, S.; Huhtikangas, A., Photochem. Photobiol., 1990, 51, 515-518; Hirata, K.; Duangteraprecha, S.; Morihara, E.; Honda, M.; Akagi, T.; Nakae, M.; Katayama, M.; Miyamoto, K., Biotech. Lett., 1997, 79, 53-57; Duangteraprecha, S.; Hirato, K.; Morihara, E.; Nakae, M.; Katayama, H.; Honda, M.; Miyamoto, K.; J. Ferment. Bioeng., 1997, 83, 227.
35. (17) Photochemical: Huhtikangas, A.; Pennanen, S.; Lounasmaa, M.; 1989, PCT Int. WO89 12 056 Chem. Abstr., 1990, 112, 198,880; Pennanen, S.; Huhtikangas, A., Photochem. Photobiol., 1990, 51, 515-518; Hirata, K.; Duangteraprecha, S.; Morihara, E.; Honda, M.; Akagi, T.; Nakae, M.; Katayama, M.; Miyamoto, K., Biotech. Lett., 1997, 79, 53-57; Duangteraprecha, S.; Hirato, K.; Morihara, E.; Nakae, M.; Katayama, H.; Honda, M.; Miyamoto, K.; J. Ferment. Bioeng., 1997, 83, 227.
36. (17) Photochemical: Huhtikangas, A.; Pennanen, S.; Lounasmaa, M.; 1989, PCT Int. WO89 12 056 Chem. Abstr., 1990, 112, 198,880; Pennanen, S.; Huhtikangas, A., Photochem. Photobiol., 1990, 51, 515-518; Hirata, K.; Duangteraprecha, S.; Morihara, E.; Honda, M.; Akagi, T.; Nakae, M.; Katayama, M.; Miyamoto, K., Biotech. Lett., 1997, 79, 53-57; Duangteraprecha, S.; Hirato, K.; Morihara, E.; Nakae, M.; Katayama, H.; Honda, M.; Miyamoto, K.; J. Ferment. Bioeng., 1997, 83, 227.
37. (18) Electrochemical: Tabakovic, I.; Gunic, E.; Juranic, I., J. Org. Chem., 1997, 62, 947-952.
38. (19) Enzymatic: Misawa, M.; Endo, T.; Goodbody, A.; Vukovic, J.; Chapple, C.; Choi, L.; Kutney, J. P., Phytochemistry, 1988, 27, 1355-1359; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R.; Heterocycles, 1988, 27, 613-620; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R., Heterocycles, 1988, 27, 621-628; Endo, T.; Goodbody, A.; Vukovic, J.; Misawa, M., Phytochemistry, 1988, 27, 2147-2149.
39. (19) Enzymatic: Misawa, M.; Endo, T.; Goodbody, A.; Vukovic, J.; Chapple, C.; Choi, L.; Kutney, J. P., Phytochemistry, 1988, 27, 1355-1359; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R.; Heterocycles, 1988, 27, 613-620; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R., Heterocycles, 1988, 27, 621-628; Endo, T.; Goodbody, A.; Vukovic, J.; Misawa, M., Phytochemistry, 1988, 27, 2147-2149.
40. (19) Enzymatic: Misawa, M.; Endo, T.; Goodbody, A.; Vukovic, J.; Chapple, C.; Choi, L.; Kutney, J. P., Phytochemistry, 1988, 27, 1355-1359; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R.; Heterocycles, 1988, 27, 613-620; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R., Heterocycles, 1988, 27, 621-628; Endo, T.; Goodbody, A.; Vukovic, J.; Misawa, M., Phytochemistry, 1988, 27, 2147-2149.
41. (19) Enzymatic: Misawa, M.; Endo, T.; Goodbody, A.; Vukovic, J.; Chapple, C.; Choi, L.; Kutney, J. P., Phytochemistry, 1988, 27, 1355-1359; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R.; Heterocycles, 1988, 27, 613-620; Kutney, J. P.; Boulet, C. A.; Choi, L. S. L.; Gustowski, W.; McHugh, M.; Nakano, J.; Nikaido, T.; Tsukamoto, H.; Hewitt, G. M.; Suen, R., Heterocycles, 1988, 27, 621-628; Endo, T.; Goodbody, A.; Vukovic, J.; Misawa, M., Phytochemistry, 1988, 27, 2147-2149.
42. (20) Andriamialasoa, R. Z.; Langlois, N.; Langlois, Y.; Potier, P.; Blandon, P., Can. J. Chem., 1979, 57, 2572-2577;
43. 4 reductive workup indicates a mixture of 3-4 and 4-5 elimination; Cherney, R. J. Ph.D. Thesis, University of Virginia, 1990.
44. (22) Mangeney, P.; Costa, R.; Langlois, N.; Potier, P., Compte rendu Acad. Sci., Ser. C., 1977, 701-703; Andriamialisoa, R. Z.; Langlois, Y.; Langlois, N.; Potier, P.; Compte rendu Acad. Sci., Ser. C., 1977, 284, 751-754; Honma, Y.; Ban, Y., Tetrahedron Lett., 1978, 155-158.
45. (22) Mangeney, P.; Costa, R.; Langlois, N.; Potier, P., Compte rendu Acad. Sci., Ser. C., 1977, 701-703; Andriamialisoa, R. Z.; Langlois, Y.; Langlois, N.; Potier, P.; Compte rendu Acad. Sci., Ser. C., 1977, 284, 751-754; Honma, Y.; Ban, Y., Tetrahedron Lett., 1978, 155-158.
46. (22) Mangeney, P.; Costa, R.; Langlois, N.; Potier, P., Compte rendu Acad. Sci., Ser. C., 1977, 701-703; Andriamialisoa, R. Z.; Langlois, Y.; Langlois, N.; Potier, P.; Compte rendu Acad. Sci., Ser. C., 1977, 284, 751-754; Honma, Y.; Ban, Y., Tetrahedron Lett., 1978, 155-158.
47. (23) Sundberg, R. J.; Gadamasetti, K.; Hunt, P. J., Tetrahedron, 1992, 48, 277-296.
48. 4 which had incorporated an ethoxy group. The instability of this material has precluded a definitive structural assignment. Many features of the spectrum are consistent with epoxidation at C15-C20 and C16-C21 cleavage with an ethoxy substituent at C21.
49. 3+ (ref 16) describe the behavior of catharanthine alone.
50. (26) Gueritte, F.; Langlois, N.; Langlois, Y.; Sundberg, R. J.; Bloom, J. D., J. Org. Chem., 1981, 46, 5393-5395.
51. (27) Raucher, S.; Bray, B. L.; Lawrence, R. F., J. Am. Chem. Soc., 1987, 109, 442-446.
52. (28) Tabakovic, I.; Gunic, E.; Gasic, M. J., J. Chem. Soc., Perkin Trans. 2, 1996, 2741-2745.
53. (29) Roffia, S.; Conciallini, V.; Paradisi, C.; Meran, F.; Vianello, E., J. Electroanal. Chem., 1991, 302, 115-129; Maran, F., J. Am. Chem. Soc., 1993, 115, 6557-6563.
54. (29) Roffia, S.; Conciallini, V.; Paradisi, C.; Meran, F.; Vianello, E., J. Electroanal. Chem., 1991, 302, 115-129; Maran, F., J. Am. Chem. Soc., 1993, 115, 6557-6563.
55. (30) Tabakovic, I.; Tabakovic, K., Tetrahedron Lett., 1996, 37, 3659-3662.
56. (31) Kondo, T.; Matsuda, T.; Funae, Y. Jpn Kokai Tokkyo Koho JP61 3645 Chem. Abstr. 1987, 106, 17912d.
57. (32) Prepared from methyl acrylate following the method of Ho, T.-L.; Gupta, B. G. B.; Olah, G. A. Synthesis 1977, 676-677.
58. (33) Moody, C. J.; Rahimtoola, K. F. J. Chem. Soc. Perkin Trans. 1 1990, 673-679.
59. (34) Marvel, C. S.; Dec, J.; Cooke, H. G., Jr.; Cowan, J. C. J. Am. Chem. Soc. 1940, 62, 3495-3498.
60. (35) This procedure differs from that of Szantay et.al (ref. 16d) in not including one equivalent of HCl. The measured pH of the reaction mixtures was near 2.
61. (36) Nicholson, R. S.; Shain, I., Anal. Chem., 1964, 36, 706-723.
62. (37) Bard, A. J.; Faulkner, L. R., Electrochemical Methods, Fundamentals and Applications, Wiley: New York, 1980, p. 222.