Efficient functionalizations of a pyranosido-pyrimidine scaffold

Tetrahedron

Volumn 65, Issue 4, 2009, Pages 896-902

  Samb, Issa ^a   Pellegrini Moïse, Nadia ^a   Lamandé Langle, Sandrine ^a   Chapleur, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDOMIMETIC AGENT; PYRANOSIDE; PYRIMIDINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; MICROWAVE RADIATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 57649094182     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.029     Document Type: Article

References (52)

1. Belanger P.C., and Dufresne C. Can. J. Chem. 64 (1986) 1514-1520
2. Moitessier N., Minoux H., Maigret B., Chrétien F., and Chapleur Y. Lett. Pept. Sci. 5 (1998) 75-78
3. Moitessier N., Dufour S., Chrétien F., Thiery J.-P., Maigret B., and Chapleur Y. Bioorg. Med. Chem. 9 (2001) 511-523
4. Sofia M.J., Hunter R., Chan T.Y., Vaughan A., Dulina R., Wang H., and Gange D. J. Org. Chem. 63 (1998) 2802-2803
5. Peri F., Nicotra F., Leslie C.P., Micheli F., Seneci P., and Marchioro C. J. Carbohydr. Chem. 22 (2003) 57-71
6. La Ferla B., Bugada P., Cipolla L., Peri F., and Nicotra F. Eur. J. Org. Chem. 11 (2004) 2451-2470
7. Cipolla L., Peri F., Ferla B.L., Redaelli C., and Nicotra F. Curr. Org. Synth. 2 (2005) 153-173
8. Velter I., La Ferla B., and Nicotra F. J. Carbohydr. Chem. 25 (2006) 97-138
9. Hirschmann R. Angew. Chem., Int. Ed. Engl. 30 (1991) 1278-1301
10. Hirschmann R., Nicolaou K.C., Pietranico S., Salvino J., Leahy E.M., Sprengeler P.A., Furst G., Smith III A.B., Strader C.D., Cascieri M.A., Candelore M.R., Donaldson C., Vale W., and Maechler L. J. Am. Chem. Soc. 114 (1992) 9217-9218
11. Papageorgiou C., Haltiner R., Bruns C., and Petcher T. J. Bioorg. Med. Chem. Lett. 2 (1992) 135-140
12. Le Diguarher T., Boudon A., Elwell C., Paterson D.E., and Billington D.C. Bioorg. Med. Chem. Lett. 6 (1996) 1983-1988
13. Nicolaou K.C., Trujillo J.I., and Chibale K. Tetrahedron 53 (1997) 8751-8778
14. Wessel H.P., Banner D., Gubernator K., Hilpert K., Muller K., and Tschopp T. Angew. Chem., Int. Ed. 36 (1997) 751-752
15. Dinh T.Q., Smith C.D., Du X., and Armstrong R.W. J. Med. Chem. 41 (1998) 981-987
16. Hanessian S., Saavedra O.M., Xie F., Amboldi N., and Battistini C. Bioorg. Med. Chem. Lett. 10 (2000) 439-442
17. Murphy P.V., O'Brien J.L., Gorey-Foret L.J., and Smith III A.B. Tetrahedron 59 (2003) 2259-2271
18. Locardi E., Boer J., Modlinger A., Schuster A., Holzmann B., and Kessler H. J. Med. Chem. 46 (2003) 5752-5762
19. Moitessier N., Henry C., Aubert N., and Chapleur Y. Tetrahedron Lett. 46 (2005) 6191-6194
20. For recent uses of multicyclic sugar scaffolds, see:
21. Abrous L., Hynes Jr. J., Friedrich S.R., Smith III A.B., and Hirschmann R. Org. Lett. 3 (2001) 1089-1092
22. Forni E., Cipolla L., Caneva E., La Ferla B., Peri F., and Nicotra F. Tetrahedron Lett. 43 (2002) 1355-1357
23. La Ferla B., Cardona F., Perdiga I., and Nicotra F. Synlett (2005) 2641-2642
24. Cervi G., Peri F., Battistini C., Gennari C., and Nicotra F. Bioorg. Med. Chem. 14 (2006) 3349-3367
25. Mari S., Canada F.J., Jimenez-Barbero J., Bernardi A., Marcou G., Motto I., Velter I., Nicotra F., and La Ferla B. Eur. J. Org. Chem. 13 (2006) 2925-2933
26. Cacciarini M., Menichetti S., Nativi C., and Richichi B. Curr. Org. Synth. 4 (2007) 47-57
27. Chapleur Y. J. Chem. Soc., Chem. Commun. (1983) 141-142
28. Chapleur Y., and Euvrard M.N. J. Chem. Soc., Chem. Commun. (1987) 884-885
29. Mayon P., Euvrard M.N., Moufid N., and Chapleur Y. J. Chem. Soc., Chem. Commun. (1994) 399-401
30. Peseke K., Feist H., and Cuny E. Carbohydr. Res. 230 (1992) 319-325
31. Kuhla B., Peseke K., Thiele G., and Michalik M. J. Prakt. Chem. 342 (2000) 240-244
32. Ruiz R.M., Martinez I.O., Michalik M., Reinke H., Suarez J.Q., and Peseke K. J. Carbohydr. Chem. 23 (2004) 337-351
33. Kordian M., Feist H., Kantlehner W., Michalik M., and Peseke K. Z. Naturforsch 61B (2006) 406-412 and references cited therein
34. Samb I., Pellegrini-Moïse N., and Chapleur Y. Tetrahedron Lett. 48 (2007) 7978-7981
35. Haines A.H. Adv. Carbohydr. Chem. Biochem. 33 (1976) 11-101
36. David S., and Hanessian S. Tetrahedron 41 (1985) 643-663
37. Pedretti V., Mallet J.M., and Sinaÿ P. Carbohydr. Res. 244 (1993) 247-257
38. Halcomb R.L., Boyer S.H., Wittman M.D., Olson S.H., Denhart D.J., Liu K.K.C., and Danishefsky S.J. J. Am. Chem. Soc. 117 (1995) 5720-5749
39. Savarin C., Srogl J., and Liebeskind L.S. Org. Lett. 2 (2000) 3229-3231
40. Savarin C., Srogl J., and Liebeskind L.S. Org. Lett. 3 (2001) 91-93
41. Kusturin C.L., Liebeskind L.S., and Neumann W.L. Org. Lett. 4 (2002) 983-985
42. Savarin C., Srogl J., and Liebeskind L.S. Org. Lett. 4 (2002) 4309-4312
43. Liebeskind L.S., and Srogl J. Org. Lett. 4 (2002) 979-981
44. Alphonse F.-A., Suzenet F., Keromnes A., Lebret B., and Guillaumet G. Synlett (2002) 447-450
45. Egi M., and Liebeskind S.L. Org. Lett. 5 (2003) 801-802
46. Alphonse F.-A., Suzenet F., Keromnes A., Lebret B., and Guillaumet G. Org. Lett. 5 (2003) 803-805
47. Oumouch S., Bourotte M., Schmitt M., and Bourguignon J.-J. Synthesis (2005) 25-27
48. Leconte N., Pellegatti L., Tatibouet A., Suzenet F., Rollin P., and Guillaumet G. Synthesis (2007) 857-864
49. Oda H., Kobayashi T., Kosugi M., and Migita T. Tetrahedron 51 (1995) 695-702
50. Labadie J.-W., and Stille J.K. J. Am. Chem. Soc. 105 (1983) 6129-6137
51. Stulgies B., Prinz P., Magull J., Rauch K., Meindl K., Rühl S., and de Meijere A. Chem.-Eur. J 11 (2005) 308-320
52. Capella L., Degl'Innocenti A., Mordini A., Reginato G., Ricci A., and Seconi G. Synthesis (1991) 1201-1204