On the synthesis of protopine alkaloids

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7301-7306

  Wada, Yasuhiro ^a   Kaga, Harumi ^a,b   Uchiito, Shiho ^a   Kumazawa, Eri ^a   Tomiki, Miho ^a   Onozaki, Yu ^a   Kurono, Nobuhito ^a   Tokuda, Masao ^a   Ohkuma, Takeshi ^a   Oríto, Kazuhiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METHYLENE GROUP; PROTOPINE ALKALOIDS; STERIC EFFECTS;

CYCLIZATION; OXYGENATION; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

1 (2 BROMOBENZYL) 3 BENZAZEPIN 2 ONE DERIVATIVE; ALKALOID; BENZAZEPINE DERIVATIVE; PROTOPINE; PROTOPINE DERIVATIVE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; OXYGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

BENZAZEPINES; BENZOPHENANTHRIDINES; BERBERINE ALKALOIDS;

EID: 34548756080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071038y     Document Type: Article

References (67)

1. (a) Kametani, T. The Chemistry of the Isoquinoline Alkaloids; Hirokawa: Tokyo, and Elsevier: Amsterdam, 1968.
2. (b) Kametani, T. The Chemistry of the Isoquinoline Alkaloids Vol. 2; The Sendai Institute of Heterocyclic Chemistry: Japan, 1974.
3. A recent report for the minor alkaloids, see: (c) Chang, Y. C. Planta Med. 2003, 69, 148-152.
4. (a) Shamma, M. The Isoquinoline Alkaloids; Academic Press, Inc.: New York, 1972; pp 344-358.
5. (b) Onda, M.; Takahashi, H. The Alkaloids; Brossi, A., Ed.; Academic Press, Inc.: San Diego, 1988; Vol. 2, pp 181-209.
6. (a) Akbarov, Z. S.; Aliev, K. U.; Sultanov, M. B. Farmakol. Prir. Veschestv 1978, 11-29.
7. (b) Burtsev, V. N.; Dormidontov, E. N.; Salyaev, V. N. Kardiologiiya 1978, 18, 76-79.
8. (c) Burtsev, V. N.; Dormidontov, E. N.; Saliaev, V. N. Kardiologiia 1978, 18, 76-79.
9. (d) Lu, Z. A.; Wan, D. C.; Chen, Z. H.; Wang, X. H. Chin. Pharm. J. 1992, 30, 81-84.
10. (e) Zipes, D. P. Heart Disease, 5th ed.; W. B. Saunders: Philadelphia, 1997; pp 593-639.
11. (f) Song, L.-S.; Ren, G.-J.; Chen, Z.-L.; Chen, Z.-H.; Zhou, Z.-N.; Chen, H. Br. J. Pharmacol. 2000, 129, 893-900.
12. Casar, G.; Bilgehan, H.; Gözler, T. Microbiol. Bull. 1981, 15, 105-109.
13. Yue, K.-L. Acta Pharmacol. Sin. 1981, 2, 16-18.
14. (a) Ko, F. N.; Wu, T. N.; Lu, S. T.; Wu, Y. C.; Huang, T. F.; Teng, C. M. Thromb. Res. 1989, 56, 289-298.
15. (b) Shiomoto, H.; Matsuda, H.; Kubo, M. Chem. Pharm. Bull. 1990, 38, 2320-2322;
16. Chem. Pharm. Bull. 1991, 39, 474-477.
17. (c) Teng, C. M.; Ko, F. N.; Wang, J. P.; Liu, C. N.; Wu, T. S.; Chan, C. C.; Huang, T. F. J. Pharm. Pharmacol. 1991, 43, 667-669.
18. (d) Shen, Z. Q.; Chen, Z. H.; Duan, L. Acta Pharm. Sinica 1999, 20, 338-340.
19. (a) Ko, F. N.; Wu, T. N.; Lu, S. T.; Wu, Y. C.; Huang, T. F.; Teng, C. M. Jpn. J. Pharmacol. 1992, 58, 1-9.
20. (b) Grantham, C. J.; Cannell, M. B. Circ. Res. 1996, 79, 184-200.
21. Üstünes, L.; Laekeman, G. M.; Gözler, T.; Vlietinck, A. J.; Özer, A.; Herman, A. G. J. Nat. Prod. 1988, 51, 1021-1022.
22. Saeed, S. A.; Gilani, A. H.; Majoo, R. A.; Shah, B. H. Pharmacol. Res. 1997, 36, 1-7.
23. (a) Montilla, M. P.; Cabo, J.; Navarro, M. C.; Risco, S.; Jimenez, R. S.; Aneiros, J. Phytother. Res. 1990, 4, 212-215.
24. (b) Gilani, A. H.; Janbaz, K. H. Gen. Pharmacol. 1995, 26, 309-315, 619-623.
25. (c) Gilani, A. H.; Janbaz, K. H.; Shah, B. H. Pharmacol. Res. 1998, 37, 31-35.
26. (e) Janbaz, K. H.; Saeed, S. A.; Gilani, A. H. Pharmacol. Res. 1998, 38, 215-219.
27. (a) Haworth, R. D.; Perkin, W. H., Jr. J. Chem. Soc. 1926, 445, 1769-1784.
28. (b) Haworth, R. D.; Koepfli, J. B.; Perkin, W. H., Jr. J. Chem. Soc. 1927, 2261-2265.
29. (c) Russell, P. B. J. Am. Chem. Soc. 1956, 78, 3115-3121.
30. (d) Giacopello, D.; Deulofeu, V.; Comin, J. Tetrahedron 1964, 20, 2971-2975.
31. (e) Giacopello, D.; Deulofeu, V. Tetrahedron Lett. 1966, 2859-2861.
32. (f) Giacopello, D.; Deulofeu, V.; Tetrahedron 1967, 23, 3265-3269.
33. (g) Sotelo, R. M.; Giacopello, D. Aust. J. Chem. 1972, 25, 385-392.
34. (h) Kurlkarni, B. K.; Dhar, R. K.; de Souza, N. J. J. Heterocycl. Chem. 1990, 27, 623-626.
35. Bentley, K. W.; Murray, A. W. J. Chem. Soc. 1963, 2497-2501.
36. Hanaoka, M.; Mukai, C.; Arata, Y. Heterocycles 1976, 4, 1685-1686.
37. Ronsch, H. Z. Chem. 1987, 27, 64-65.
38. (a) Teitel, S.; Borgese, J.; Brossi, A. Helv. Chim. Acta 1973, 56, 553-557.
39. (b) Vesely, Z.; Holubek, J.; Kopecká, H.; Trojánek, J. Collect. Czech. Chem. Commun. 1975, 40, 1403-1410.
40. Leonard, N. J.; Sauers, R. R. J. Org. Chem. 1957, 22, 63-65.
41. Nalliah, B.; Manske, R. H. F.; Rodrigo, R. Tetrahedron Lett. 1974, 19, 1765-1768.
42. Castedo, L.; Peralta, A.; Puga, A.; Saa, J. M.; Suau, R. Heterocycles 1986, 24, 5-7.
43. Tani, C.; Kiyoshi, T. Chem. Pharm. Bull. 1974, 22, 2457-2459.
44. (a) Takao, N.; Iwasa, K.; Kamiguchi, M.; Makiko, S. Chem. Pharm. Bull. 1976, 24, 2859-2968.
45. (b) Takao, N.; Kamiguchi, M.; Okada, M. Helv. Chim. Acta 1983, 66, 473-484.
46. (c) Iwasa, K.; Tomii, A.; Takao, N. Heterocycles 1984, 22, 33-38.
47. (d) Iwasa, K.; Tomii, A.; Takao, N.; Ishida, T.; Inoue, M. J. Chem. Res., Synop. 1985, 1, 16-17.
48. (a) Onto, K.; Itoh, M. J. Chem. Soc., Chem. Commun. 1978, 813-814.
49. (b) Orito, K.; Kudoh, S.; Yamada, K.; Itoh, M. Heterocycles 1980, 14, 11-14.
50. (c) Orito, K.; Kurokawa, Y.; Itoh, M. Tetrahedron 1980, 36, 617-621.
51. Orito, K.; Uchiito, S.; Satoh, Y.; Tatsuzawa, T.; Harada, R.; Tokuda, M. Org. Lett. 2000, 2, 307-310.
52. Orito, K.; Miyazawa, M.; Kanbayashi, R.; Tokuda, M.; Suginome, H. J. Org. Chem. 1999, 64, 6583-6596.
53. Orito, K.; Kaga, H.; Itoh, M.; de Silva, O. S.; Manske, R. H.; Rodrigo, R. J. Heterocycl. Chem. 1980, 417-423.
54. (a) Cushman, M.; Dekow, F. W. Tetrahedron 1978, 34, 1435-1439.
55. (b) de Silva, S. O.; Ahmad, I.; Snieckus, V. Can. J. Chem. 1979, 57, 1598-1605.
56. Orito, K.; Manske, R. H.; Rodrigo, R. J. Am. Chem. Soc. 1974, 96, 1944-1945.
57. Rhodes, R. A.; Boykin, D. W. Synth. Commun. 1988, 18, 681-687.
58. Bonwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Homan, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551-2553.
59. Wang, X. M.; Tan, J.; Grozinger, K. Tetrahedron Lett. 1998, 39, 6609-6612.
60. Valpuesta, M.; Diaz, A.; Torres, G.; Suau, R. Tetrahedron 2002, 58, 5053-5059.
61. Kametani, T.; Ihara, M.; Honda, T. J. Chem. Soc. C 1970, 1060-1064.
62. Sha, C.-K.; young, J.-J.; Yeh, C.-P.; Chang, S.-C.; Wang, S.-L. J. Org. Chem. 1991, 56, 2694-2696.
63. Yakimov, G.; Mollov, N.; Left, J. E.; Guinaudeau, H.; Freyer, A. J.; Shamma, M. J. Nat. Prod. 1984, 47, 1048-1049.
64. For the synthesis by transformation of a spirobenzylisoquinoline alkaloid, fumaricine, see: Blascó, G. Acta Chim. Hung. 1991, 128, 819-822.
65. Giese, M. W.; Moser, W. H. J. Org. Chem. 2005, 70, 6222-6229.
66. Naik, R. G.; Wheeler, T. S. J. Chem. Soc. 1938, 1780-1783.
67. Olivera, R.; SanMartin, R.: Dominguez, E.; Solans, X.; Urtiaga, M. K.; Arriortua, M. I. J. Org. Chem. 2000, 65, 6398-6411.