C-Nucleosides Derived from Simple Aromatic Hydrocarbons

Synlett

Volumn 1997, Issue 4, 1997, Pages 341-347

  Chaudhuri, Narayan C ^a,d,e,f   Ren, Rex X F ^a,b,g,h,i   Kool, Eric T ^a,b,c  

^a UNIVERSITY OF ROCHESTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^d UNIVERSITY OF CALCUTTA   (India)

^e INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^f UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^g WUHAN UNIVERSITY   (China)

^h Wuhan University ^*

ⁱ UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002577181     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-788     Document Type: Article

References (57)

1. For reviews of C-glycoside synthesis, see: (a) Hanessian, S.; Pernet, A. G. Adv. Carbo. Chem. Biochem. 1976, 33, 111-188. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
2. For reviews of C-glycoside synthesis, see: (a) Hanessian, S.; Pernet, A. G. Adv. Carbo. Chem. Biochem. 1976, 33, 111-188. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
3. (a) Lerch, U.; Burdon, M. G.; Moffat, J. G. J. Org. Chem. 1971, 36, 1507;
4. (b) Brown, D. M.; Burdon, M. G.; Slatcher, R. P. J. Chem. Soc., Section C 1968, 1051;
5. (c) Shapiro, R.; Chambers, R. W. J. Am. Chem. Soc. 1961, 83, 3920.
6. (a) Kalvoda, L; Farkas, J; Sorm, F. Tetrahedron Lett. 1970, 2297;
7. (b) Trummlitz, G.; Moffat, J. G. J. Org. Chem. 1973, 38, 1841;
8. (c) Barton, D. H. R.; Ramesh, M. J. Am. Chem. Soc. 1990, 112, 891.
9. Buchanan, J. G.; Jumaah, A. O.; Kerr, G.; Talekar, R. R.; Wightman, R. H. J., Chem. Soc., Perkins Trans. 1 1991, 1077.
10. Farkas, J.; Flegelova, Z; Sorm, F. Tetrahedron Lett. 1972, 2279.
11. (a) Casiraghi, G.; Cornia, M.; Rassu, G.; Sante, C.D.; Spanu, P. Tetrahedron 1992, 48, 5619;
12. (b) Patil, S.A.; Otter, B. A.; Klein, R.S. Tetrahedron Lett. 1994, 35, 5339.
13. (a) Yokoyama, M.; Tanabe, T.; Toyoshima, A.; Togo, H. Synthesis 1993, 517;
14. (b) Yokoyama, M.; Toyoshima, A.; Akiba, T; Togo, H. Chem. Lett. 1994, 265;
15. (c) Dondoni, A.; Marra, A.; Sherrmann, M.C. Tetrahedron Lett. 1993, 34, 7323;
16. (d) Yokoyama, M.; Akiba, T.; Togo, H. Synthesis 1995, 638.
17. (a) Belmans, M.; Esmans, E.; Dommisse, R.; Lepoivre, J.; Alderweireldt, F.; Balzarini, J.; Clercq, E. D. Nucl. & Nucleotides 1985, 4, 523;
18. (b) Mertes, M. P.; Zielinki, J.; Pillar, C. J. Med. Chem. 1967, 10, 320;
19. (c) Togo, H; Ishigami, S.; Fujii, M.; Ikuma, T.; Yokoyama, M. J. Chem. Soc. Perkin Trans. 1 1994, 2931.
20. (a) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232;
21. (b) Togo, H; Aoki, M.; Kuramochi, T.; Yokoyama, M. J. Chem. Soc. Perkin Trans. 1 1993, 2417.
22. Bergstrom, D. E.; Zhang, P. Tetrahedron Lett. 1991, 32, 6485.
23. (a) Buchanan, J. G.; Quijano, M. L.; Wightman, R. H. J. Chem. Soc. Perkins Trans. 1 1992, 1573;
24. (b) Zhang, H. C.; Brakta, M.; Daves, G. D. Jr. Nucleosides & Nucleotides 1995, 14, 105.
25. (a) Du, J.; Qu, F.; Lee, D.; Newton, M.G.; Chu, C. K. Tetrahedron Lett. 1995, 36, 8167;
26. (b) Dondoni, A.; Scherrmann, M. C. Tetrahedron Lett. 1993, 34, 7319;
27. (c) Dondoni, A.; Scherrmann, M. C. J. Org. Chem. 1994, 59, 6404.
28. Ren, X.-F.; Schweitzer, B. A.; Sheils, C. J.; Kool, E. T. Angew. Chem. 1996, 35, 743.
29. Puglisi, J. D.; Chen, L.; Blanchard, S.; Frankel, A. D. Science 1995, 270, 1200 and references cited therein.
30. (a) Miller, T. R.; Hopkins, P. B. Bioorg. & Med. Chem.Lett. 1994, 4, 981;
31. (b) Miller, T. R.; Alley, S. C.; Reese, A. W.; Solomon, M. S.; McCallister, W. V.; Mailer, C.; Robinson, B. H.; Hopkins, P. B. J. Am. Chem. Soc. 1995, 117, 9377.
32. (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238; ibid. 1995, 60, 8326;
33. (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238; ibid. 1995, 60, 8326;
34. (b) Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863.
35. Schweitzer, B. A.; Sheils, C. J.; Ren, X.-F.; Chaudhuri, N. C.; Kool, E. T. J. Biomol. Struct. Dyn. 1996, 209.
36. Ren, R. X.-F.; Chaudhuri, N. C.; Paris, P. L.; Rumney IV, S.; Kool, E. T. J. Am. Chem. Soc., 1996, 118, 7671.
37. Millican, T. A.; Mock, G. A.; Chauncey, M. A.; Patel, T. P.; Eaton, M. A. W.; Gunning, J.; Cutbush, S. D.; Neidle, S.; Mann, J. Nucleic Acids Res. 1984, 12, 7435.
38. Klein, R. S.; Kotick, M. P.; Watanabe, K. A.; Fox, J. J. J. Org. Chem. 1971, 36, 4113.
39. Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1988, 29, 6935.
40. Hoffer, M. Chem. Ber. 1960, 93, 2111.
41. Hurd, C. D.; Miles, H. T. J. Org. Chem. 1964, 29, 2976.
42. (a) Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 1795;
43. (b) Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 4910.
44. Robins, M. J.; Robins, R. K. J. Am. Chem. Soc. 1965, 87, 4934.
45. (a) Srivastava, P. C.; Robins, P. K.; Takusagawa, F.; Berman, H. M. J. Het.Chem. 1981, 18, 1659;
46. (b) Hacksell, U.; Cheng, J. C-Y.; Daves, G. D. Jr. J. Carbohydr. Chem. 1986, 5, 287.
47. Smith, M.; Jardetzky, C. D. J. Mol. Spectroc. 1968, 28, 70.
48. (a) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205;
49. (b) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333.
50. Francois, P.; Sonveaux, E.; Touillaux, R. Nucleosides & Nucleotides 1990, 9, 379.
51. Ford, K. G.; Neidle, S.; Eaton, M. A. W.; Millican, T. A.; Mann, J. Acta. Cryst. 1987, C43, 1988.
52. Karplus, M. J. Chem. Phys. 1959, 30, 11.
53. Angyal, S. J. Angew. Chem. Int. Ed. Engl. 1969, 8, 157.
54. Cleve, G.; Hoyer, G.; Schulz, G.; Vorbruggen, H. Chem. Ber. 1973, 106, 3062.
55. Senior, M.; Jones, R. A.; Breslauer, K. J. Proc. Natl. Acad. Sci. USA 1988, 85, 6242.
56. Guckian, K. M.; Schweitzer, B. A.; Ren, X.-F.; Sheils, C. J.; Paris, P. L.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182.
57. Moran, S.; Ren, X.-F.; Sheils, C. J.; Kool, E. T. Nucleic Acids Res. 1996, 24, 2044.