Bioactive montanine derivatives from halide-induced rearrangements of haemanthamine-type alkaloids. Absolute configuration by VCD

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1491-1494

  Cedrón, Juan C ^a,b   Estévez Braun, Ana ^a,b   Ravelo, Ángel G ^a,b   Gutiérrez, David ^c   Flores, Ninoska ^c   Bucio, María A ^d   Pérez Hernández, Nury ^e   Joseph Nathan, Pedro ^d  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b Madrid Spain   (Spain)

^c UNIVERSIDAD MAYOR DE SAN ANDRÉS   (Bolivia)

^d DEPARTAMENTO DE FÍSICA   (Mexico)

^e UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMARYLLIDACEAE ALKALOID; ANTIMALARIAL AGENT; FUSED HETEROCYCLIC RINGS; HAEMANTHAMINE; ISOQUINOLINE DERIVATIVE; MONTANINE; PANCRACINE; PHENANTHRIDINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; DRUG EFFECT; ISOMERISM; PLASMODIUM FALCIPARUM; SYNTHESIS;

ALKALOIDS; AMARYLLIDACEAE ALKALOIDS; ANIMALS; ANTIMALARIALS; CIRCULAR DICHROISM; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; ISOMERISM; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENANTHRIDINES; PLASMODIUM FALCIPARUM;

EID: 64349106550     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900065x     Document Type: Article

References (29)

1. Hoshino, O. The Amaryllidaceae Alkaloids. In The Alkaloids: Chemistry and Biology; Cordell, G., Ed.; Academic Press: New York, 1998.
2. (b) Martin, S. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, Chapter 2.
3. Lewis, J. Nat. Prod. Rep 2000, 1757, and previous reviews in the series.
4. Cedrón, J. C., Oberti, J. C., Estévez-Braun, A.; Ravelo, A. G.; Del Arco-Aguilar, M.; López, M. J. Nat. Prod. 2009, 72, 112.
5. Labraña, J.; King'Ori, A.; Kricsfalusy, V.; Brun, R.; Codina, C., Viladomat, F.; Bastida, J. Phytochemistry 2002, 60, 847.
6. (a) Bastida, J.; Lavilla, R.; Viladomat, F. Chemical and Biological Aspects of Narcissus Alkaloids. In The Alkaloids; Cordell, G., Ed.; Elsevier: New York, 2006; Vol. 63, p 87.
7. (b) Southon, I.; Buckingham, J. Dictionary of Alkaloids; Chapman and Hall: London, 1989.
8. (c) Antoun, M. D.; Mendoza, N. T.; Rios, Y. R.; Proctor, G. R.; Wickramaratne, D. B.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 1993, 56, 1423.
9. (a) Pandey, G.; Banerjee, P.; Kumar, R.; Puranik, V. G. Org. Lett. 2005, 7, 3713.
10. (b) Banwell, M. G.; Edwards, A. J.; Jolliffe, K. A.; Kemmler, M. J Chem. Soc. Perkin. Trans. 1 2001, 1345.
11. (c) Banwell, M. G.; Kokas, O. J.; Willis, A. C. Org. Lett. 2007, 9, 3503.
12. (d) Sha, C., Hong, A.; Huang, C. Org. Lett. 2001, 3, 2177.
13. (e) Hong, A.; Cheng, T.; Raghukumar, V.; Sha, C. J. Org. Chem. 2008, 73, 7580.
14. (f) Overman, L. E.; Shim, J. J. Org. Chem. 1991, 56, 5005.
15. (g) Pearson, W. H.; Lian, B. W. Angew. Chem., Int. Ed. 1998, 37, 1724.
16. (h) Jin, J.; Weinreb, S. M. J. Am. Chem. Soc. 1997, 119, 5773.
17. (i) Ikeda, M.; Hamada, M.; Yamashita, T.; Matsui, K.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin. Trans. 1 1999, 1949.
18. (j) Ishizaki, M.; Kurihara, K.; Tanazawa, E.; Hoshino, O. J. Chem. Soc, Perkin Trans. 1 1993, 101.
19. The configuration at C-11 is 11R in 5. See: Wildman, W. C., Clardy, J. C., Hauser, F. M.; Dahm, D.; Jacobon, R. A. J. Am. Chem. Soc. 1970, 92, 6337.
20. Bastida, J.; Viladomat, F.; Llabres, J. M.; Codina, C., Feliz, M.; Rubiralta, M. Phytochemistry 1987, 26, 1519.
21. For a 3D structure of 5, see Supporting Information.
22. Inubushi, Y.; Fales, H. M.; Warnhoff, E. W.; Wildman, W. C. J. Org. Chem. 1960, 25, 2153.
23. (a) Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Chirality 2003, 15, 743.
24. (b) Nafie, L. A. Nat. Prod. Commun. 2008, 3, 451.
25. (a) Cerda-Garcia-Rojas, C. M.; Catalán, C. A.; Muro, A. C., Joseph-Nathan, P. J. Nat. Prod. 2008, 71, 967.
26. (b) Min, H.; Aye, M.; Taniguchi, T.; Miura, N.; Monde, K.; Ohzawa, K.; Nikai, T.; Niwa, M.; Takaya, Y. Tetrahedron Lett. 2007, 48, 6155.
27. (c) Muñoz, M. A.; Muñoz, O.; Joseph-Nathan, P. J. Nat. Prod. 2006, 69, 1335.
28. Cerda-García-Rojas, C. M.; García-Gutiérrez, H. A.; Hernández-Hernández, J. D.; Román-Marín, L. U.; Joseph-Nathan, P. J. Nat. Prod. 2007, 70, 1167.
29. Labraña, J.; Machocho, A.; Kricsfalusy, V.; Brun, R.; Codina, C., Viladomat, F.; Bastida, J. Phytochemistry 2002, 60, 847.