Novel synthetic route to the tricyclic core of (±)-galanthamine

Tetrahedron Letters

Volumn 50, Issue 34, 2009, Pages 4882-4884

  Chandrasekhar, S ^a   Basu, Debjit ^a   Sailu, M ^a   Kotamraju, S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

GALANTAMINE; ISOVANILLIN;

ALKYLATION; ARTICLE; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; OZONOLYSIS;

EID: 67650034627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.055     Document Type: Article

References (40)

1. Hoshino O. In: Cordell G.A. (Ed). The Alkaloids Vol. 51 (1998), Academic Press, New York 323
2. Proskurnina N.F., and Yakoleva A.P. J. Gen. Chem. 22 (1952) 1899
3. Marco-Contelles J., Carreiras M.D., Rodriguez C., Villarroya M., and Garcia A.G. Chem. Rev. 106 (2006) 116
4. Sramek J.J., Frackiewicz E.J., and Cutler N.R. Expert Opin. Invest. Drugs 9 (2000) 2393
5. Mucke H.A.M. Drugs Today 33 (1997) 259
6. Irwin R.L., and Smith H.J. Biochem. Pharmacol. 3 (1960) 147
7. Bretagne M., and Valletta J. Anesth. Analg. (Paris) 22 (1965) 285
8. Sacco K., Creeden C., Reutenauer E., and George T. Schizophrenia Res. 103 (2008) 326
9. Han S., Sweeney J.E., and Joullie M.M. Eur. J. Med. Chem. 27 (1992) 673
10. Valverde O., Maldonado R., and Kieffer B.L. CNS Drugs 10 (1998) 1
11. Hudlicky T., Butora G., Fearnley S.P., Gum A.G., and Stabile M.R. Stud. Nat. Prod. Chem. 18 (1996) 43
12. Vanlaer S., Borggraeve W.M.D., and Compernolle F. Eur. J. Org. Chem. (2007) 4995
13. Marco L., and Carreiras M.C. Recent Patents CNS Drugs Disc. 1 (2006) 105
14. Hemetsberger M., Treu M., Hametner C., Jordis U., Mereiter K., and Johannes F. Heterocycles 63 (2004) 2217
15. Treu M., and Jordis U. Molecules 7 (2002) 374
16. Pelish H.E., Westwood N.J., Feng Y., Kirchhausen T., and Shair M.D. J. Am. Chem. Soc. 123 (2001) 6740
17. Missoum A., Sinibaldi M.E., Vallée-Goyet D., and Jean-Claude G. Synth. Commun. 27 (1997) 453
18. Vlahov R., Krikorian D., Spassov G., Chinova M., Vlahov I., Parushev S., Snatzke G., Ernst L., Kieslich K., Abraham W., and Sheldrick W.S. Tetrahedron 45 (1989) 3329
19. Satcharoen V., McLean N.J., Kemp S.C., Nicholas P.C., and Brown R. Org. Lett. 9 (2007) 1867
20. Marco-Contelles J., Carreiras M.C., Rodri{dotless}́guez C., Villarroya M., and Garci{dotless}́ A.G. Chem. Rev. 106 (2006) 116
21. Trost B.M., Tang W., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 14785
22. Kodama S., Hamashima Y., Nishide K., and Node M. Angew. Chem., Int. Ed 43 (2004) 2659
23. Trost B.M., and Tang W. Angew. Chem., Int. Ed. 14 (2002) 2795
24. Node M., Kodama S., Hamashima Y., Baba T., Hamamichi N., and Nishide K. Angew. Chem., Int. Ed. 40 (2001) 3060
25. Trost B.M., and Toste F.D. J. Am. Chem. Soc. 122 (2000) 11262
26. Czollner L., Frantsits W., Bernhard K., Hedenig U., Johannes F., and Jordis U. Tetrahedron Lett. 39 (1998) 2087
27. Krikorian D., Vlahov R., Parushdev S., Chinova M., and Vlahov I. Tetrahedron Lett. 25 (1984) 2969
28. Krikorian D., Tarpanov V., Parushdev S., and Mechkarov P. Synth. Commun. 30 (2000) 2833
29. Barton D.H.R., and Kirby G.W. J. Chem. Soc. (C) (1969) 2602
30. Barton D.H.R., Kirby G.W., and Taylor J.B. J. Chem. Soc. (1962) 4545
31. Schultz A.G., Yee Y.K., and Berger M.H. J. Am. Chem. Soc. 99 (1977) 8065
32. Fan C.A., Tu Y.Q., Song Z.L., Zhang E., Shi L., Wang M., Wang B., and Zhang S.Y. Org. Lett. 6 (2004) 4691
33. Ishizaki M., Ozaki K., Kanematsu A., Isoda T., and Hoshino O. J. Org. Chem. 58 (1993) 3877
34. Gras E., Guillou C., and Thal C. Tetrahedron Lett. 40 (1999) 9243
35. Sanchez I.H., Soria J.J., Lopez F.J., Larraza M.I., and Flores H.J. J. Org. Chem. 49 (1984) 157
36. Martin S.F., and Garrison P.J. J. Org. Chem. 47 (1982) 1513
37. Ackland D.J., and Pinhey J.T. J. Chem. Soc., Perkin Trans. 1 (1987) 2695
38. +
39. Ellman G.L., Courtney K.D., Andres Jr. V., and Featherstone R.M. Biochem. Pharmacol. 7 (1961) 88
40. Decker M. Eur. J. Med. Chem. 40 (2005) 305