Enantiodivergent synthesis of cyclohexenyl nucleosides

Journal of Organic Chemistry

Volumn 74, Issue 6, 2009, Pages 2425-2432

  Ferrer, Èric ^a   Alibés, Ramon ^a   Busqué, Félix ^a   Figueredo, Marta ^a   Font, Josep ^a   De March, Pedro ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-HIV ACTIVITIES; CYCLOHEXENYL NUCLEOSIDES; ENANTIOPURE; NUCLEOSIDE ANALOGUES;

NUCLEOTIDES;

2 CYCLOHEXENONE DERIVATIVE; BENZOIN; CYCLOHEX 2 EN 1,4 DIONE; NUCLEOSIDE DERIVATIVE; PURINE NUCLEOSIDE DERIVATIVE; PYRIMIDINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

ANTI-HIV AGENTS; BENZOIN; CYCLOHEXENES; NUCLEOSIDES; PURINES; PYRIMIDINES;

EID: 64149128175     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802492g     Document Type: Article

References (39)

1. (a) Wang, J.; Jin, Y.; Rapp, K. L.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2007, 50, 1828-1839.
2. (b) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235-250.
3. (c) Agrofoglio, L. A.; Challand, S. R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publishers: Dordrecht, 1998.
4. (d) Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272.
5. Coates, J. A. V.; Inggall, H. J.; Pearson, B. A.; Penn, C. R.; Storer, R.; Williamson, C.; Cameron, J. M. Antiviral Res. 1991, 15, 161-168.
6. Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; St. Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Domsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082-1093.
7. (a) Wang, J.; Froeyen, M.; Herdewijn, P. Adv. Antivir. Drug Des. 2004, 4, 119-145, and references cited therein.8.
8. (b) Vijgen, S.; Nauwelaerts, K.; Wang, J.; Van Aerschot, A.; Lagoja, I.; Herdewijn, P. J. Org. Chem. 2005, 70, 45914597.
9. (c) Horváth, A.; Ruttens, B.; Herdewijn, P. Tetrahedron Lett. 2007, 48, 3621-3623.
10. Herdewijn, P.; De Clercq, E. Bioorg. Med. Chem. Lett. 2001, 11, 15911597.
11. Wang, J.; Froeven, M.; Hendrix, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 2000, 43, 736-745.
12. (a) ferry, B. J.; Cianci, C. W.; Hagen, M. E. Mol. Pharm. 1991, 40, 591-596.
13. (b) Schinazi, R. F.; Chu, C. K.; Peck, A.; McMillan, A.; Mathis, R.; Cannon, D.; Jeong, L.- S.; Beach, J. W.; Choi, W.-B.; Yeola, S.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 672-676.
14. (c) Wang, P.; Gullen, B.; Newton, M. G.; Cheng, Y. C.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 1999, 42, 3390-3399.
15. (a) de March, P.; Escoda, M.; Figueredo, M.; Font, J.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1997, 62, 7781-7787.
16. (b) de March, P.; Escoda, M.; Figueredo, M.; Font, J.; Mediano, J. An. Quim., Int. Ed. 1997, 93, 81-87.
17. (c) de March, P.; Figueredo, M.; Font, J.; Rodríguez, S. Tetrahedron 2000, 56, 3603-3609.
18. (d) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Rodríguez, S. Tetrahedron: Asymmetry 2001, 12, 3077-3080.
19. (a) Busqué, F.; Cantó, M.; de March, P.; Figueredo, M.; Font, J.; Rodriguez, S. Tetrahedron: Asymmetry 2003, 14, 2021-2032.
20. (b) Alibés, R.; Bayón, P.; de March, P.; Figueredo, M.; Font. .J.; Marjanet, G. Qrg. Lett. 2006, 8, 1617-1620.
21. (c) Alibés, R.; Busqué, F.; Bardaji, G.-G.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 2006, 17, 2632-2636.
22. de March, P.; Escoda, M.; Figueredo, M.; Font, J.; García- García, E.; Rodríguez, S. Tetrahedron: Asymmetry 2000, 11, 4473-4483.
23. Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem., Int. Ed. 2002, 41, 993-996.
24. (a) Mukaiyama, T.; Matsuo, J.-I.; Kitagawa, H. Chem. Lett. 2000, 12501251.
25. (b) Matsuo, J.; Iida, D.; Tatani, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 223-234.
26. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012, and references cited therein.
27. Pérez-Pérez, M.-J.; Rozenski, J.; Bussom, R.; Herdewijn, P. J. Org. Chem. 1995, 60, 1531-1537.
28. (a) Garner, P.; Ramakanth, S. J. Org. Chem. 1982, 53, 1294-1298.
29. (b) Rustullet, A.; Alibés, R.; de March, P.; Figueredo, M.; Font, J. Org. Lett. 2007, 9, 2827-2830.
30. Trost, B. M.; Madsen, R.; Guile, S. D.; Brown, B. J. Am. Chem. Soc. 2000, 122, 5947-5956.
31. (a) Rosenquist, Å.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282-6288.
32. (b) Konkel, M. J.; Vince, R. Tetrahedron 1996, 52, 799-808.
33. Ramesh, K.; Wolfe, M. S.; Lee, Y.; Velde, D. V.; Borchardt, R. T. J. Org. Chem. 1992, 57, 5861-5868.
34. Cruickshank, K. A.; Jiricny, J.; Reese, C. Tetrahedron Lett. 1984, 25, 681-684.
35. (a) Yamada, K.; Sakata, S.; Yoshimura, Y. J. Org. Chem. 1998, 63, 6891-6899.
36. (b) Wang, J.; Viña, D.; Busson, R.; Herdewijn, P. J. Org. Chem. 2003, 68, 4499-4505.
37. (c) Wang, J.; Jin, Y.; Rapp, K. L.; Bennett, M.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2005, 48, 3736-3748.
38. Frieden, M.; Giraud, M.; Reese, C. B.; Song, Q. J. Chem. Soc., Perkin Trans. 1 1998, 2827-2832.
39. Ahn, H.; Choi, T. H.; de Castro, K.; Lee, K. C.; Kim, B.; Moon, B. S.; Hong, S. H.; Lee, J. C.; Chun, K. S.; Cheon, G. J.; Lim, S. M.; An, G. I.; Rhee, H. J. Med. Chem. 2007, 50, 6032-6038.