Synthesis of novel nucleosides with a fused cyclopropane ring substituted by a hydroxymethyl group

Tetrahedron

Volumn 56, Issue 19, 2000, Pages 2995-3003

  Lescop, Cyrille ^a   Huet, François ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

Bicyclic nucleosides; Ring contraction; Stereoselection; Substitution

Indexed keywords

NUCLEOSIDE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HYDROXYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034607840     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00174-5     Document Type: Article

References (46)

1. For recent reviews see for instance: (a) Agrofoglio, L. A.; Challand, S. R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publisher: Dordrecht, Boston, London, 1998.
2. (b) Herdewijn, P. Drug Discovery Today 1997, 2, 235.
3. (c) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
4. For bicyclic nucleosides with a skeleton different from oxabicyclo[3.1.0]hexane see for example: (a) Moon, H. R.; Kim, H. O.; Chun, M. W.; Jeong, L. S.; Marquez, V. E. J. Org. Chem. 1999, 64, 4733.
5. (b) Chao, Q.; Nair, V. Tetrahedron 1997, 53, 1957.
6. (c) Ezzitouni, A.; Marquez, V. E. J. Chem. Soc., Perkin Trans. 1 1997, 1073.
7. (d) Bolli, M.; Lubini, P.; Leumann, C. Helv. Chim. Acta 1995, 78, 2077.
8. (e) Björsne, M.; Szabo, T.; Samuelsson, B.; Classon, B. Nucleosides Nucleotides 1995, 14, 279.
9. (f) Papchikhin, A.; Agback, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1995, 51, 329.
10. (g) Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331.
11. (h) Tarkoy, M.; Leumann, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 1432.
12. (i) Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi Jr., J. J. Tetrahedron Lett. 1993, 34, 6233.
13. (j) Tarkoy, M.; Bolli, M.; Schweizer, B.; Leumann, C. Helv. Chim. Acta 1993, 76, 481.
14. (a) Hong, J. H.; Chun, B. K.; Chu, C. K. Tetrahedron Lett. 1998, 39, 225.
15. (b) Sard, H. Nucleosides Nucleotides 1994, 13, 2321.
16. (c) Okabe, M.; Sun, R.-C. Tetrahedron Lett. 1989, 30, 2203.
17. (d) Beard, A. R.; Butler, P. I.; Mann, J.; Partlett, N. K. Carbohydr. Res. 1990, 205, 87.
18. (e) Wu, J.-C.; Chattopadhyaya, J. Tetrahedron 1990, 46, 2587.
19. (a) Sasaki, T.; Minamoto, K.; Suzuki, H. J. Org. Chem. 1973, 38, 598.
20. (b) Kawana, M.; Kuzuhara, H. Nucleosides Nucleotides 1992, 11, 551.
21. (c) Adachi, T.; Iwasaki, T.; Miyoshi, M.; Inoue, I. J. Chem. Soc., Chem. Commun. 1977, 248.
22. (a) Grangier, G.; Aitken, D. J.; Guillaume, D.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 4355.
23. (b) Wu, J.-C.; Chattopadhyaya, J. Tetrahedron 1989, 45, 4507.
24. (c) Tong, W.; Xi, Z.; Gioeli, C.; Chattopadhyaya, J. Tetrahedron 1991, 47, 3431.
25. (d) Haly, B.; Bharadwaj, R.; Sanghvi, Y. S. Synlett 1996, 687.
26. (e) Yannopoulos, C. G.; Zhou, W.-Q.; Nower, P.; Peoc'h, D.; Sanghvi, Y. S.; Just, G. Synlett 1997, 378.
27. Mévellec L., Huet F. Tetrahedron. 53:1997;5797.
28. (a) Brauman, J. I.; Archie Jr., W. C. J. Am. Chem. Soc. 1972, 94, 4262.
29. (b) Bloomfield, J. J.; Owsley, D. C. Org. Photochem. Synth. 1976, 2, 36.
30. (c) Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S. T.; Turner, R. W.; Wallace, T. W. Tetrahedron 1992, 48, 515.
31. (d) Gauvry, N.; Comoy, C.; Lescop, C.; Huet, F. Synthesis, 1999, 574.
32. (a) Soai, K.; Yokoyama, S.; Mochida, K. Synthesis 1987, 647.
33. (b) Binns, F.; Hayes, R.; Hodgetts, K. J.; Saengchantara, S. T.; Wallace, T. W.; Wallis, C. J. Tetrahedron 1996, 42, 3631.
34. (c) Mévellec, L.; Evers, M.; Huet, F. Tetrahedron 1996, 48, 15103.
35. See for instance Pretch, E.; Clerc, T.; Seibl, J.; Simon, W. Tables of Spectral Data for Structure Determination of Organic Compounds, 2nd ed.; Springer-Verlag: Berlin, Heidelberg, 1989.
36. (a) Conia, J.-M.; Salaün, J. Acc. Chem. Res. 1972, 5, 33.
37. (b) Conia, J.-M.; Robson, M. J. Angew. Chem., Int. Ed. Engl. 1975, 14, 473.
38. (c) Gorzynski Smith, J. Synthesis 1984, 629.
39. (d) Mévellec, L.; Huet F. Tetrahedron Lett. 1995, 41, 7441.
40. (e) Gauvry, N.; Huet, F. Tetrahedron 1999, 55, 1321.
41. Okabe M., Sun R.-C., Tam S.Y.-K., Todaro L.J., Coffen D.L. J. Org. Chem. 53:1988;4780.
42. (a) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
43. (b) Vorbrüggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279.
44. Dudycz L.W., Wright G.E. Nucleosides Nucleotides. 3:1984;33.
45. Robins M.J., Zou R., Guo Z., Wnuk S.F. J. Org. Chem. 61:1996;9207. (and references cited therein).
46. Abdel-Rahman A.A.-H., Zahran M.A., Abdel-Megied A.E.-S., Pedersen E.B., Nielsen C. Synthesis. 1996;237.