Synthesis of annelated pyranosides: a rapid and efficient entry to highly functionalized optically pure branched-pyrazoles

Tetrahedron Letters

Volumn 48, Issue 45, 2007, Pages 7978-7981

  Samb, Issa ^a   Pellegrini Moïse, Nadia ^a   Chapleur, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

Pyranosides; Pyrazoles; Ring pyran opening; Scaffold

Indexed keywords

HYDROXYL GROUP; METHANOL; PYRANOSIDE; PYRAZOLE DERIVATIVE;

ACIDITY; ALKYLATION; ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; MOLECULAR MIMICRY; RING OPENING;

EID: 35148853583     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.048     Document Type: Article

References (30)

1. Belanger P.C., and Dufresne C. Can. J. Chem. 64 (1986) 1514-1520
2. Hirschmann R. Angew. Chem., Int. Ed. Engl. 30 (1991) 1278-1301
3. 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
4. Cipolla L., Peri F., Ferla B.L., Redaelli C., and Nicotra F. Curr. Org. Synth. 2 (2005) 153-173 and references cited therein
5. Moitessier N., Minoux H., Maigret B., Chrétien F., and Chapleur Y. Lett. Pept. Sci. 5 (1998) 75-78
6. Moitessier N., Dufour S., Chrétien F., Thiery J.P., Maigret B., and Chapleur Y. Bioorg. Med. Chem. 9 (2001) 511-523
7. La Ferla B., Cardona F., Perdiga I., and Nicotra F. Synlett (2005) 2641-2642
8. Cervi G., Peri F., Battistini C., Gennari C., and Nicotra F. Bioorg. Med. Chem. 14 (2006) 3349-3367
9. Chapleur Y. Chem. Commun. 3 (1983) 141-142
10. Chapleur Y., and Euvrard M.N. Chem. Commun. 12 (1987) 884-885
11. Mayon P., Euvrard M.N., Moufid N., and Chapleur Y. Chem. Commun. 4 (1994) 399-401
12. Genin M.J., Biles C., Keiser B.J., Poppe S.M., Swaney S.M., Tarpley W.G., Yagi Y., and Romero D.L. J. Med. Chem. 43 (2000) 1034-1040
13. Price M.L., and Jorgensen W.L. J. Am. Chem. Soc. 122 (2000) 9455-9466
14. Elguero J. In: Katritsky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1996), Pergamon Press, Oxford 1-75
15. Kost A.N., and Grandberg I.I. Adv. Heterocycl. Chem. 6 (1966) 347-429
16. Katritzky A.R., Wang M., Zhang S., Voronkov M.V., and Steel P.J. J. Org. Chem. 66 (2001) 6787-6791
17. Rosati O., Curini M., Marcotullio M.C., Macchiarulo A., Perfumi M., Mattioli L., Rismondo F., and Cravotto G. Bioorg. Med. Chem. 15 (2007) 3463-3473
18. Lee K.Y., Gowrisankar S., and Kim J.N. Tetrahedron Lett. 46 (2005) 5387
19. Wang Z., and Qin H. Green Chem. 6 (2004) 90-92
20. Peseke K., Feist H., and Cuny E. Carbohydr. Res. 230 (1992) 319-325
21. Kuhla B., Peseke K., Thiele G., and Michalik M. J. Prakt. Chem. 342 (2000) 240-244
22. Methling K., Kopf J., Michalik Ma., Reinke H., Buerger C., Oberender H., and Peseke K. J. Carbohydr. Chem. 22 (2003) 537-548
23. Ruiz R.M., Martinez I.O., Michalik M., Reinke H., Suarez J.Q., and Peseke K. J. Carbohydr. Chem. 23 (2004) 337-351
24. Otero I., Methling K., Feist H., Michalik M., Quincoces J., Reinke H., and Peseke K. J. Carbohydr. Chem. 24 (2005) 809-829
25. +.
26. Tarrago G., Ramdani A., Elguero J., and Espada M. J. Heterocycl. Chem. 17 (1980) 137-142
27. Malhotra N., Falt-Hansen B., and Becher J. J. Heterocycl. Chem. 28 (1991) 1837-1839
28. Montoya V., Pons J., Branchadell V., and Ros J. Tetrahedron 61 (2005) 12377-12385
29. +.
30. +.