Synthesis of cyclopropyl-fused carbocyclic nucleosides via the regioselective opening of cyclicsulfi sulfites

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4733-4741

  Moon, Hyung Ryong ^a   Kim, Hea Ok ^b   Chun, Moon Woo ^c   Jeong, Lak Shin ^b   Marquez, Victor E ^d  

^a Ewha Womans University   (South Korea)

^b Kyungin Women's University   (South Korea)

^c Seoul National University   (South Korea)

^d NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE DERIVATIVE; CARBOCYCLIC NUCLEOSIDE; CYTOSINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; URACIL DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0001257247     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990010m     Document Type: Article

References (44)

1. Marquez, V. E.; Lim, M.-I. Med. Res. Rev 1986, 6, 1.
2. Bothwick, A. D.; Biggadike, K. Tetrahedron 1982, 48, 571.
3. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
4. Marquez, V. E. Carbocyclic Nucleosides. In Advances in Antiviral Drug Design; Vol 2, De Clercq, E., Ed., Jai Press: Greenwich, Connecticut, USA, 1996; Vol. 2, pp 89-146.
5. Kalman, A.; Koritzanszky, T.; Beres, J.; Sagi, G. Nucleosides Nucleotides 1990, 8, 1121.
6. Kishi, T.; Moroui, M.; Nishikawa, M.; Kamiya, K.; Mizuno, K. J. Chem. Soc. Chem. Commun. 1967, 852.
7. Highcock, R. M.; Hilpert, H.; Myers, P. L.; Roberts, S. M.; Storer, R. J. Chem. Soc., Perkin Trans 1 1991, 1127.
8. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8320.
9. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
10. Wang, Z.; Quiocho, F. A. Biochemistry 1998, 37, 8314.
11. Wang, S.; Milne, G. W. A.; Nicklaus, M. C.; Marquez, V. E.; Lee, J.; Blumberg, P. M. J. Med. Chem. 1994, 37, 1326.
12. Shimada, N.; Hasegawa, S.; Harada, T.; Tomisawa, T.; Fujii, A.; Takita, T. J. Antibiot. 1988, 39, 1623.
13. Nakamura, H.; Hasegawa, S.; Shimada, N.; Fujii, A.; Takita, T.; Iitaka, Y. J. Antibiot. 1986, 39, 1626.
14. Norbeck, D. W.; Kern, E.; Hayashi, S.; Rosenbrook, W.; Sham, H.; Herrin, T.; Plattner, J. J.; Erikson, J.; Clement, J.; Swanson, R.; Shipkowtz, N.; Hardy, D.; Marsh, K.; Arnett, G.; Shannon, W.; Broder, S.; Mitsuya, H. J. Med. Chem. 1990, 33, 1281.
15. Hayashi, S. Norbeck, D. W.; Rosenbrook, W.; Fine, R. L.; Matsukura, M.; Plattner, J. J.; Broder, S.; Mitsuya, H. Antimicrob. Agents Chemother. 1990, 34, 287.
16. Nishiyama, Y.; Yamamoto, N.; Yamada, Y.; Daikoku, T.; Ishikawa, Y.-I.; Takahashi, K. J. Antibiot. 1989, 42, 1854.
17. Slusarchyk, W. A.; Young, M. G.; Bisachi, G. S.; Hocksetin, D. R.; Zahler, R. Tetrahedron Lett. 1989, 30, 6453.
18. Tseng, C. K.-H.; Marquez, V. E.; Milne, G. W. A.; Wysocki, R. J., Jr.; Mitsuya, H.; Shirasaki, T.; Driscoll, J. S. J. Med. Chem. 1991, 10, 291.
19. Sterzycki, R. Z.; Martin, J. C.; Wittman, M.; Brankovan, V.; Yang, H.; Hitchcock, M. J.; Mansuri, M. M. Nucleosides Nucleotides 1991, 10, 291.
20. Boumchita, H.; Legraverend, M.; Bisagni, E. Heterocycles 1991, 32, 1785.
21. Buenger, G.; Marquez, V. E. Tetrahedron Lett. 1992, 33, 3707.
22. Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi, J. J., Jr. Tetrahedron Lett. 1993, 34, 6233.
23. Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331.
24. Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J., Jr. J. Med. Chem. 1994, 37, 3389.
25. (a) Lohray, B. B. Synthesis 1992, 1035.
26. (b) Lohray, B. B.; Ahuha, J. R. J. Chem. Soc., Chem. Commun. 1991, 95.
27. Gao, Y.; Zepp, C. M. Tetrahedron Lett. 1991, 32, 3155.
28. Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markiva, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709.
29. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. Chem. Commun. 1987, 1625.
30. Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M. Tetrahedron Lett 1989, 30, 1483.
31. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
32. Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
33. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1980, 53, 230.
34. David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
35. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans 1 1975, 1574.
36. Ko, S. Y. J. Org. Chem. 1995, 60, 6250.
37. Lang, H.; Moser, H. E. Helv. Chim. Acta 1994, 77, 1527.
38. Marquez, V. E.; Ezzitouni, A.; Russ, P.; Siddiqui, M. A.; Ford, H., Jr.; Feldman, R. J.; Mitsuya, H.; George, C.; Barchi, J. J., Jr. J. Am. Chem. Soc. 1998, 120, 2780.
39. Shealy, Y. F.; O'dell, C. A. J. Heterocycl. Chem. 1976, 13, 1015.
40. Divakar, K. J.; Reese, C. B. J. Chem. Soc., Perkin Trans 1 1982, 1171.
41. (a) Bannal, C.; Chavis, C.; Lucas, M. J. Chem. Soc., Perkin Trans 1 1994, 1401.
42. (b) Jenny, T. F.; Horlacher, J.; Previsani, N.; Benner, S. A. Helv. Chim. Acta 1992, 75, 1944.
43. Siddiqui, M. A.; Ford, H., Jr.; George, C.; Marquez, V. E. Nucleosides Nucleotides 1996, 15, 235.
44. Crimmins, M. T. Tetrahedron 1998, 54, 9229.