An efficient route to acyclic C-nucleosides and fused-ring analogues of uridine from exo-glycals

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8388-8391

  Enderlin, Gérald ^a   Taillefumier, Claude ^a,b   Didierjean, Claude ^c   Chapleur, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

^c Nancy University CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; C-NUCLEOSIDES; CHEMICAL EQUATIONS; EXO-GLYCALS; IMINOSUGARS; MITSUNOBU CONDITION; NITROGEN ATOM; SUBSTITUTED URACILS;

AMINES; CHEMICAL REACTIONS; ESTERS; SUGAR (SUCROSE); SUGARS;

BIOMOLECULES;

ACYCLIC NUCLEOSIDE; BETA AMINO ACID; C NUCLEOSIDE; ESTER DERIVATIVE; FUSED ALICYCLIC COMPOUND; GLYCAN DERIVATIVE; IMINOSUGAR; NITROGEN; URACIL DERIVATIVE; URIDINE DERIVATIVE;

ARTICLE; ATOM; CYCLIZATION; MITSUNOBU REACTION; SUBSTITUTION REACTION;

MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOSIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; URIDINE;

EID: 70350714289     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901604w     Document Type: Article

References (57)

1. (a) El Alaoui, A. M.; Faraj, A.; Pierra, C.; Boudou, V.; Johnson, R.; Mathe, C.; Gosselin, G.; Korba, B. E.; Imbach, J.-L.; et al. Antiviral Chem. Chemother. 1996, 7, 276.
2. (b) Gumina, G.; Olgen, S.; Chu, C. K. Antiviral Nucleosides 2003, 77.
3. (c) De Clercq, E.; Holy, A. Nat. Rev. Drug Discov. 2005, 4, 928.
4. (d) Piperno, A.; Chiacchio, M. A.; Iannazzo, D.; Romeo, R. Curr. Med. Chem. 2006, 13, 3675.
5. (e) Kaur, H.; Babu, B. R.; Maiti, S. Chem. Rev. 2007, 107, 4672.
6. (a) Modified Nucleosides; Herdewijn, P., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
7. (b) Len, C.; Mondon, M.; Lebreton, J. Tetrahedron 2008, 64, 7453.
8. (c) Mathé, C.; Périgaud, C. Eur. J. Org. Chem. 2008, 2008, 1489.
9. (d) Choi, Y.; Moon, H. R.; Yoshimura, Y.; Marquez, V. E. Nucleosides, Nucleotides & Nucleic Acids 2003, 22, 547.
10. (e) Mieczkowski, A.; Peltier, P.; Zevaco, T.; Agrofoglio, L. A. Tetrahedron 2009, 65, 4053.
11. (a) Holy, A. Antiviral Res. 2006, 71, 248.
12. (b) Amblard, F.; Nolan, S. P.; Agrofoglio, L. A. Tetrahedron 2005, 61, 7067.
13. (c) Khandazhinskaya, A.; Yasko, M.; Shirokova, E. Curr. Med. Chem. 2006, 13, 2953.
14. (d) De Clercq, E. Antiviral Res. 2007, 75, 1.
15. Shaban, M. A. E.; Nasr, A. Z. The Chemistry of C-Nucleosides and Their Analogs I: C-Nucleosides of Hetero Monocyclic Bases. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, CA, 1997; Vol.68, pp 223-432. (Pubitemid 127819558)
16. (a) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
17. (b) Rodriguez, J. B.; Comin, M. J. Mini Rev. Med. Chem. 2003, 3, 95.
18. (a) Nakajima, M.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamori, M.; Haneishi, T. J. Antibiot. 1991, 44, 293.
19. (b) Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2005, 70, 6369.
20. (a) Kittaka, A.; Asakura, T.; Kuze, T.; Tanaka, H.; Yamada, N.; Nakamura, K. T.; Miyasaka, T. J. Org. Chem. 1999, 64, 7081.
21. (b) Gimisis, T.; Castellari, C. J. Chem. Soc., Chem. Commun. 1997, 2089.
22. (c) Estevez, J. C.; Burton, J. W.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Dwek, R. A.; Brown, D.; Fleet, G. W. Tetrahedron: Asymmetry 1998, 9, 2137.
23. (d) Alvarez, R.; Jimeno, M.-L.; Gago, F.; Balzarini, J.; Perez-Perez, M.-J.; Camarasa, M.-J. Antiviral Chem. Chemother. 1998, 9, 333.
24. (e) Chatgilialoglu, C.; Gimisis, T.; Spada, G. P. Chem. Eur. J. 1999, 5, 2866.
25. (f) Gasch, C.; Pradera, M. A.; Salameh, B. A. B.; Molina, J. L.; Fuentes, J. Tetrahedron: Asymmetry 2001, 12, 1267.
26. (g) Renard, A.; Lhomme, J.; Kotera, M. J. Org. Chem. 2002, 67, 1302.
27. (h) Babu, B. R.; Keinicke, L.; Petersen, M.; Nielsen, C.; Wengel, J. Org. Biomol. Chem. 2003, 1, 3514.
28. (i) Roy, A.; Achari, B.; Mandal, S. B. Tetrahedron Lett. 2006, 47, 3875.
29. (j) Sano, H.; Mio, S.; Kitagawa, J.; Sugai, S. Tetrahedron: Asymmetry 1994, 5, 2233.
30. (k) Dong, S.; Paquette, L. A. J. Org. Chem. 2006, 71, 1647.
31. (l) Tripathi, S.; Roy, B. G.; Drew, M. G. B.; Achari, B.; Mandal, S. B. J. Org. Chem. 2007, 72, 7427.
32. (a) Taillefumier, C.; Thielges, S.; Chapleur, Y. Tetrahedron 2004, 60, 2213.
33. (b) Taillefumier, C.; Chapleur, Y. Chem. Rev. 2004, 104, 263.
34. (a) Lakhrissi, M.; Chapleur, Y. Angew. Chem., Int. Ed. 1996, 35, 750.
35. (b) Lakhrissi, M.; Chapleur, Y. Synlett 1991, 583.
36. (a) Taillefumier, C.; Enderlin, G.; Chapleur, Y. Lett. Org. Chem. 2004, 1, 226.
37. (b) Enderlin, G.; Taillefumier, C.; Didierjean, C.; Chapleur, Y. Tetrahedron: Asymmetry 2005, 16, 2459.
38. For related fused ring systems see: (a) Hashimoto, M.; Matsumoto, M.; Terashima, S. Tetrahedron 2003, 59, 3041.
39. (b) Evans, P. A.; Lai, K. W.; Zhang, H.-R.; Huffman, J. C. Chem. Commun. 2006, 844.
40. (c) Yadav, L. D. S.; Rai, A.; Rai, V. K.; Awasthi, C. Synlett 2007, 1905.
41. Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327.
42. (a) Chu, C. K.; Suh, J. J. Heterocycl. Chem. 1986, 23, 1621.
43. (b) Rudloff, I.; Michalik, M.; Montero, A.; Peseke, K. Synthesis 2001, 1686.
44. (c) Chen, J.; Sambaiah, T.; Illarionov, B.; Fischer, M.; Bacher, A.; Cushman, M. J. Org. Chem. 2004, 69, 6996.
45. (d) Otero, I.; Methling, K.; Feist, H.; Michalik, M.; Quincoces, J.; Reinke, H.; Peseke, K. J. Carbohydr. Chem. 2005, 24, 809.
46. (e) Sagar, R.; Kim, M.-J.; Park, S. B. Tetrahedron Lett. 2008, 49, 5080.
47. (a) Merino, P. Curr. Med. Chem. Anti-Infective Agents 2002, 1, 389.
48. (b) Richichi, B.; Cicchi, S.; Chiacchio, U.; Romeo, G.; Brandi, A. Tetrahedron Lett. 2002, 43, 4013.
49. (c) Procopio, A.; Alcaro, S.; De Nino, A.; Maiuolo, L.; Ortuso, F.; Sindona, G. Bioorg. Med. Chem. Lett. 2005, 15, 545.
50. (d) Kocalka, P.; Pohl, R.; Rejman, D.; Rosenberg, I. Nucleosides, Nucleotides & Nucleic Acids 2005, 24, 805.
51. (e) Mannucci, V.; Cordero, F. M.; Piperno, A.; Romeo, G.; Brandi, A. Tetrahedron: Asymmetry 2008, 19, 1204.
52. (f) Yang, S.; Busson, R.; Herdewijn, P. Tetrahedron 2008, 64, 10062.
53. (a) Li, H.; Schuetz, C.; Favre, S.; Zhang, Y.; Vogel, P.; Sinay, P.; Bleriot, Y. Org. Biomol. Chem. 2006, 4, 1653.
54. (b) Markad, S. D.; Karanjule, N. S.; Sharma, T.; Sabharwal, S. G.; Dhavale, D. D. Org. Biomol. Chem. 2006, 4, 3675.
55. (c) Liu, T.; Zhang, Y.; Bleriot, Y. Synlett 2007, 905.
56. (d) Bande, O. P.; Jadhav, V. H.; Puranik, V. G.; Dhavale, D. D. Tetrahedron: Asymmetry 2007, 18, 1176.
57. (e) Otero, J. M.; Estevez, A. M.; Soengas, R. G.; Estevez, J. C.; Nash, R. J.; Fleet, G. W. J.; Estevez, R. J. Tetrahedron: Asymmetry 2008, 19, 2443.