Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses

Tetrahedron Letters

Volumn 50, Issue 50, 2009, Pages 7048-7050

  Fourrière, Gaëlle ^a   Lalot, Jérôme ^a   Hijfte, Nathalie Van ^a   Quirion, Jean Charles ^a   Leclerc, Eric ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

Carbasugars; Fluorine; Nucleosides; Radical cyclization

Indexed keywords

5 DEOXYPENTOFURANOSE; ALDEHYDE DERIVATIVE; CARBOCYCLIC NUCLEOSIDE; CARBOHYDRATE DERIVATIVE; FURAN DERIVATIVE; NUCLEOSIDE ANALOG; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; FLUORINATION; SYNTHESIS;

EID: 70350499000     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.170     Document Type: Article

References (39)

1. Agrofoglio L.A., and Challand S.R. Acyclic, Carbocyclic and L-Nucleosides (1998), Kluwer Academic Publishers, Dordrecht
2. Crimmins M.T. Tetrahedron 54 (1998) 9229-9272
3. Ferrero M., and Gotor V. Chem. Rev. 100 (2000) 4319-4348
4. Meier C., Knispel T., Marquez V.E., Siddiqui M.A., De Clercq E., and Balzarini J. J. Med. Chem. 42 (1999) 1615-1624
5. Kirsch P. Modern Fluoroorganic Chemistry (2004), Wiley-VCH, Weinheim, Germany
6. Wang J., Jin Y., Rapp K.L., Bennett M., Schinazi R.F., and Chu C.K. J. Med. Chem. 48 (2005) 3736-3748 and references cited therein
7. For the synthesis of fluorinated carbocyclic analogues of deoxypentofuranoses, see:. Barth F., and O-Yang C. Tetrahedron Lett. 32 (1991) 5873-5876
8. Arnone A., Bravo P., Cavicchio G., Frigerio M., and Viani F. Tetrahedron 48 (1992) 8523-8540
9. Yang Y.-Y., Meng W.-D., and Qing F.-L. Org. Lett. 6 (2004) 4257-4259
10. For the synthesis of fluorinated carbocyclic analogues of hexopyranoses, see:. Jiang S., Singh G., and Batsanov A.S. Tetrahedron: Asymmetry 11 (2000) 3873-3877
11. Audouard C., Fawcett J., Griffith G.A., Kérourédan E., Miah A., Percy J.M., and Yang H. Org. Lett. 6 (2004) 4269-4272
12. Deleuze A., Menozzi C., Sollogoub M., and Sinaÿ P. Angew. Chem., Int. Ed. 43 (2004) 6680-6683
13. Sardinha J., Guieu S., Deleuze A., Fernández-Alonso M.C., Rauter A.P., Sinaÿ P., Marrot J., Jiménez-Barbero J., and Sollogoub M. Carbohydr. Res. 342 (2007) 1689-1703
14. Sardinha J., Rauter A.P., and Sollogoub M. Tetrahedron Lett. 49 (2008) 5548-5550
15. Moreno B., Quehen C., Rose-Hélène M., Leclerc E., and Quirion J.-C. Org. Lett. 9 (2007) 2477-2480
16. Poulain F., Serre A.-L., Lalot J., Leclerc E., and Quirion J.-C. J. Org. Chem. 73 (2008) 2435-2438
17. Poulain F., Leclerc E., and Quirion J.-C. Tetrahedron Lett. 50 (2009) 1803-1805 and references cited therein
18. Paquette L.A., and Bailey S. J. Org. Chem. 60 (1995) 7849-7856
19. Hansen F.G., Bundgaard E., and Madsen R. J. Org. Chem. 70 (2005) 10139-10142
20. Uenishi J., and Ohmiya H. Tetrahedron 59 (2003) 7011-7022
21. Moutel S., Shipman M., Martin O.R., Ikeda K., and Asano N. Tetrahedron: Asymmetry 16 (2005) 487-491
22. For the addition to aromatic or poorly functionalized aliphatic aldehydes, see:. Qin Y.-Y., Qiu X.-L., Yang Y.-Y., Meng W.-D., and Qing F.-L. J. Org. Chem. 70 (2005) 9040-9043
23. Prakash G.K.S., Hu J., Wang Y., and Olah G. J. Fluorine Chem. 126 (2005) 527-532
24. Sugimoto H., Nakamura S., Shibata Y., Shibata N., and Toru T. Tetrahedron Lett. 47 (2006) 1337-1340
25. Mizuta S., Shibata N., Ogawa S., Fujimoto H., Nakamura S., and Toru T. Chem. Commun. (2006) 2575-2577
26. Pohmakotr M., Boonkitpattarakul K., Ieawsuwan W., Jarussophon S., Duangdee N., Tuchinda P., and Reutrakul V. Tetrahedron 62 (2006) 5973-5985
27. Pohmakotr M., Panichakul D., Tuchinda P., and Reutrakul V. Tetrahedron 63 (2007) 9429-9436
28. For the cyclization of difluoromethyl radicals, see:. Cavicchio G., Marchetti V., Arnone A., Bravo P., and Viani F. Tetrahedron 47 (1991) 9439-9448
29. Morikawa T., Kodama Y., Uchida J., Takano M., Washio Y., and Taguchi T. Tetrahedron 48 (1992) 8915-8926
30. Buttle L.A., and Motherwell W.B. Tetrahedron Lett. 35 (1994) 3995-3998
31. Arnone A., Bravo P., Frigerio M., Viani F., Cavicchio G., and Crucianelli F. J. Org. Chem. 59 (1994) 3459-3466
32. Qin Y.-Y., Yang Y.-Y., Qiu X.-L., and Qing F.-L. Synthesis (2006) 1475-1479
33. Li Y., and Hu J. Angew. Chem., Int. Ed. 46 (2007) 2489-2492
34. Beckwith A.L.J. Tetrahedron 37 (1981) 3073-3100
35. Spellmeyer D.C., and Houk K.N. J. Org. Chem. 52 (1987) 959-974
36. Bar G., and Parsons A.F. Chem. Soc. Rev. 32 (2003) 251-263
37. The addition of fluoroalkylsilane reagents to α-chiral aldehydes is often poorly diastereoselective except for α-dibenzylaminoaldehydes for which a Felkin selectivity is observed:. Andrés J.M., Pedrosa R., and Pérez-Encabo A. Eur. J. Org. Chem. (2004) 1558-1566
38. Liu J., Ni C., Wang F., and Hu J. Tetrahedron Lett. 49 (2008) 1605-1608
39. Lavaire S., Plantier-Royon R., and Portella C. Tetrahedron: Asymmetry 9 (1998) 213-226