Synthesis of Amaryllidaceae alkaloids, siculine, oxocrinine, epicrinine, and buflavine

Tetrahedron

Volumn 60, Issue 22, 2004, Pages 4901-4907

  Kodama, Sumiaki ^a   Takita, Hirofumi ^a   Kajimoto, Tetsuya ^a   Nishide, Kiyoharu ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Buflavine; Epicrinine; Oxocrinine; Phenol coupling; Phenyliodine(III) bis(trifluoroacete) (PIFA); Siculine

Indexed keywords

ALKALOID DERIVATIVE; ANTIVIRUS AGENT; BUFLAVINE; EPICRININE; OXOCRININE; PHENOL DERIVATIVE; PLANT EXTRACT; SICULINE; UNCLASSIFIED DRUG;

ACYLATION; AMINATION; ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

AMARYLLIDACEAE;

EID: 2342485821     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.03.087     Document Type: Article

References (46)

1. Hoshino O. Cordell G.A. The alkaloid. Vol. 51:1988;323-424 Academic, New York
2. Martin S.F. Brossi A. The alkaloids. Vol. 30:1987;251-376 Academic, New York
3. Irwin R.L., Smith H.J. III. Biochem. Pharmacol. 3:1960;147-148
4. Mucke H.A.M. Drugs Today. 33:1997;251-257
5. Rainer M. Drugs Today. 33:1997;273-279
6. Barton D.H.R., Kirby G.W. J. Chem. Soc. 1962;806
7. Shimizu K., Tomioka K., Yamada S., Koga K. Chem. Pharm. Bull. 26:1978;3765
8. Holton R.A., Sibi M.P., Murphy W.S. J. Am. Chem. Soc. 110:1988;314
9. Node M., Kodama S., Hamashima Y., Baba T., Hamamichi N., Nishide K. Angew. Chem. Int. Ed. 40:2001;3060
10. Kodama S., Hamashima Y., Nishide K., Node M. Angew. Chem. Int. Ed. 2004;. in press
11. Maritidine: (a) Schwartz M.A., Holton R.A. J. Am. Chem. Soc. 92:1970;1090
12. Kametani T., Kohno T., Shibuya S., Fukumoto K. Chem. Commun. 14:1971;775
13. Kametani T., Kohno T., Shibuya S., Fukumoto K. Tetrahedron. 27:1971;5441
14. Yamada S., Tomioka K., Koga K. Tetrahedron Lett. 1976;57
15. Tomioka K., Shimizu K., Yamada S., Koga K. Heterocycles. 6:1977;1752
16. Tomioka K., Koga K., Yamada S. Chem. Pharm. Bull. 25:1977;2681
17. Kita Y., Takada T., Gyoten M., Ohtsubo M., Tohma H., Zenk H.M., Eichhorn J. J. Org. Chem. 61:1996;5857
18. Kita Y., Arisawa M., Gyoten M., Nakajima M., Hamada R., Tohma H., Takada T. J. Org. Chem. 63:1998;6625
19. Oxomaritidine: (i) Kotani E., Takeuchi N., Tobinaga S. J. Chem. Soc., Chem. Commun. 1973;550
20. Kotani E., Takeuchi N., Tobinaga S. Tetrahedron Lett. 1973;2735
21. Ley S.T., Schucht O., Thomas A.W., Murray P.J. J. Chem. Soc., Perkin Trans. 1. 1999;1251
22. Bru C., Thal C., Guillou C. Org. Lett. 5:2003;1845
23. Lyle R.E., Kielar E.A., Crowder J.R., Wildman W.C. J. Chem. Soc. 82:1961;2620
24. Maxfeldt H., Schneider R.S., Mooberry J.B. J. Am. Chem. Soc. 88:1966;3670
25. Pabuccuoglu V., Richomme P., Gozler T., Kivcak B., Freyer A.J., Shamma M. J. Nat. Prod. 52:1989;785
26. Ali A.A., Sayed H.M.E., Abdallah O.M., Steiglich W. Phytochemistry. 25:1986;2399
27. Viladomat F., Bastida J., Codina C., Campbell W.E., Mathee S. Phytochemistry. 40:1955;307
28. Keck G.E., Webb R.R. J. Am. Chem. Soc. 103:1981;3137
29. Schkeryantz J.M., Pearson W.H. Tetrahedron. 52:1996;3107
30. Padwa A., Brodney M.A., Dimitroff M., Liu B., Wu T.H. J. Org. Chem. 66:2001;3119
31. Song Z.L., Wang B.M., Tu Y.Q., Fun C.A., Zhang S.Y. Org. Lett. 5:2003;2319
32. Lin L.Z., Hu S.F., Chai H.B., Pengsuparp T., Pezzuto J.M., Cordell G.A., Ruangrungsi N. Phytochemistry. 40:1995;1295
33. Viladomat F., Bastida J., Codina C., Campbell W.E., Mathee S. Phytochemistry. 40:1995;307
34. Kita Y., Tohma H., Kikuchi K., Inagaki M., Yakura T. J. Org. Chem. 56:1991;435
35. Kita Y., Gyoten M., Ohtsubo M., Thoma H., Takada T. Chem. Commun. 1996;1481
36. Kametani T., Kohno T. Tetrahedron Lett. 1971;3155
37. Sanchez I.H., Lopez F.J., Soria J.J., Larraza M.I., Flores H.J. J. Am. Chem. Soc. 105:1983;7640
38. Schwartz M.A., Rose B.F., Vishnuvajjala B. J. Am. Chem. Soc. 95:1973;612
39. Kametani T., Kohno T., Charubala R., Shibuya S., Fukumoto K. Chem. Pharm. Bull. 20:1972;1488
40. Pearson W.H., Lovering F.E. J. Org. Chem. 63:1998;3607
41. Kobayashi S., Kihara M., Shizu S., Katayama S., Ikeda H., Kitahiro K., Matsumoto H. Chem. Pharm. Bull. 25:1977;3312
42. Hoarou C., Couture A., Deniau E., Grandclaudon A. J. Org. Chem. 67:2002;5846
43. Prakash A.P., Snieckus V. Tetrahedron Lett. 39:1998;1325
44. Sahakitpichan P., Ruchirawat S. Tetrahedron Lett. 44:2003;5239
45. Takada T., Arisawa M., Gyoten M., Hamada R., Tohma H., Kita Y. J. Org. Chem. 63:1998;7698
46. Mupchan S.M., Dhingra O.P., Kim C.K. J. Org. Chem. 43:1978;4076