New telluride-mediated elimination for novel synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3725-3729

  Sheng, Jia ^a   Hassan, Abdalla E A ^a   Huang, Zhen ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COST REDUCTION; DRUG THERAPY; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ANHYDRONUCLEOSIDES; DIMETHYL DITELLURIDE; TELLURIDE INTERMEDIATE; TELLURIDE MONOANION;

NUCLEIC ACIDS;

2',3' DIDEHYDRO 2',3' DIDEOXYNUCLEOSIDE; 2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DIMETHYL DITELLURIDE; ORGANOTELLURIUM DERIVATIVE; SELENIDE; TELLURIDE;

ADDITION REACTION; ARTICLE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; SUBSTITUTION REACTION;

ANTI-HIV AGENTS; DIDEOXYNUCLEOSIDES; MOLECULAR CONFORMATION; STEREOISOMERISM; TELLURIUM;

EID: 43449127528     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7025806     Document Type: Article

References (40)

1. For a review, see: Chu, C. K., Baker, D. C., Eds. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Plenum Press: New York, 1993.
2. (a) De Clercq, E. J. Med. Chem. 1995, 38, 2491.
3. (b) Doong, S. L.; Tsai, C. H.; Schinazi, R. F.; Liotta, D. C.; Cheng, Y. C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 8495.
4. (c) Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
5. (a) Ogilvie, K. K.; Iwacha, D. J. Can. J. Chem. 1974, 52, 1787.
6. (b) Saito, Y.; Zevaco, T. A; Agrofoglio, L. A. Tetrahedron 2002, 58, 9593.
7. (c) Wiley, C. A.; Grafe, M.; Kennedy, C.; Nelson, J. A. Acta Neuropathol. (Berlin) 1988, 76, 338.
8. (d) Kikyoya, T. Jpn. Kokai Tokkyo Koho 1988, JP 63241356-A-19881006.
9. (e) Luzzio, F. A.; Menes, M. E. J. Org. Chem. 1994, 59, 7267.
10. Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
11. (a) Dudycz, L. W. Nucleosides Nucleotides 1989, 8, 35.
12. (b) Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. V. J. Org. Chem. 1989, 54, 2217.
13. (a) Josan, J. S.; Eastwood, F. W. Aust. J. Chem. 1968, 21, 2013.
14. (b) Crank, G.; Eastwood, F. W. Aust. J. Chem. 1964, 17, 1392.
15. (a) Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902.
16. (b) Mansuri, M. M.; Starrett, J. E.; Wos, J. A.; Tortolani, D. R.; Brodfuehrer, P. R.; Howell, H. G.; Martin, J. C. J. Org. Chem. 1989, 54, 4780.
17. (c) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367.
18. (a) Gillaizeau, I.; Lagoja, I. M.; Nolan, S. P.; Aucagne, V.; Rozenski, J.; Herdewijn, P; Agrofoglio, L. A. Eur. J. Org. Chem. 2003, 666.
19. (b) Ewing, D.; Glacon, V.; Mackenzie, G.; Postel, D.; Len, C. Tetrahedron Lett. 2002, 43, 3503.
20. Horwitz, J. P.; Chua, J.; Rooge, M. A. D.; Noel, R.; Klundt, I. L. J. Org. Chem. 1966, 31, 205.
21. (a) Diaz, Y.; El-Laghdach, A.; Matheu, M. I.; Castillon, S. J. Org. Chem. 1997, 62, 1501.
22. (b) Beach, J. W.; Kim, H. O.; Jeong, L. S.; Nampalli, S.; Islam, Q.; Ahn, S. K.; Babu, J. R.; Chu, C. K J. Org. Chem. 1992, 57, 3887.
23. (c) Haraguchi, K.; Tanaka. H.; Maeda, H.; Itoh, Y.; Saito, S.; Miyasaka, T. J. Org. Chem. 1991, 56, 5401.
24. Clive, D. L. J.; Wickens, P. L.; Sgarbi, P. W. M. J. Org. Chem. 1996, 61, 7426.
25. (a) Sheng, J.; Jiang, J.; Salon, J.; Huang, Z. Org. Lett. 2007, 9, 749.
26. (b) Salon, J.; Sheng, J.; Jiang, J.; Chen, G.; Caton, W, J.; Huang, Z. J. Am. Chem. Soc. 2007, 129, 4862.
27. (c) Jiang, J.; Sheng, J.; Carrasco, N.; Huang, Z. Nucleic Acids Res. 2007, 35, 477.
28. (d) Carrasco, N.; Caton-Williams, J.; Brandt, G.; Wang, S.; Huang, Z. Ang. Chem., Int. Ed. 2006, 45, 94.
29. (e) Salon, J; Chen, G.; Portilla, Y.; Germann, M. W.; Huang, Z. Org. Lett. 2005, 7, 5645.
30. (f) Carrasco, N.; Huang, Z. J. Am. Chem. Soc. 2004, 126, 448.
31. (g) Carrasco, N.; Buzin, Y.; Tyson, E.; Halpert, E.; Huang, Z. Nucleic Acids Res. 2004, 32, 1638.
32. (h) Du, Q.; Carrasco, N.; Teplova, M.; Wilds, C. J.; Egli, M.; Huang, Z. J. Am. Chem. Soc. 2002, 124, 24.
33. (i) Carrasco, N.; Ginsburg, D.; Du, Q.; Huang, Z. Nucleosides Nucleotides Nucleic Acids 2001, 20, 1723.
34. (a) Ogilvie, K. K.; Iwacha, D. J. Can. J. Chem. 1974, 52, 1787.
35. (b) Shi, J.; Du, J.; Ma, T.; Pankiewicz, K. W.; Patterson, S. E.; Tharnish, P. M.; McBrayer, T. R.; Stuyver, L. J.; Otto, M. J.; Chu, C. K.; Schinazi, R. F.; Watanabe, K. A. Bioorg. Med. Chem. 2005, 13, 1641.
36. Logue, M. W.; Han, B, H. J. Org. Chem. 1980, 45, 5000.
37. Sasaki, T.; Minamoto, K.; Sugiura, T.; Niwa, M. J. Org. Chem. 1976, 41, 3138.
38. Dunkel, M.; Cook, P. D.; Acevedo, O. L. J. Heterocycl.Chem. 1993, 30, 1421.
39. Chambert, S.; Gautier-Luneau, I.; Fontecave, M.; Decout, J. L. J. Org. Chem. 2000, 65, 249.
40. Palomino, E.; Meltsner, B, R.; Kessel, D.; Horwitz, J. P. J. Med. Chem. 1990, 33, 258.