Regioselective synthesis of β-N1- and β-N3-alloxazine nucleosides

Organic Letters

Volumn 2, Issue 2, 2000, Pages 227-230

  Wang, Zhiwei ^a   Rizzo, Carmelo J ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001563055     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9913338     Document Type: Article

References (31)

1. Millar, D. P. Curr. Opin Struct. Biol. 1996, 6, 322.
2. Pfleiderer, W. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 145-261.
3. (a) Hawkins, M. E.; Pfleiderer, W.; Belis, F. M.; Porter, D.; Knutson, J. R. Anal. Biochem. 1997, 244, 86.
4. (b) Hawkins, M. E.; Pfleiderer, W.; Mazumder, A.; Pommier, Y. G.; Balis, F. M. Nucleic Acids Res. 1995, 23, 2872,
5. (c) Jungmann, O.; Pfleiderer, W. Tetrahedron Lett. 1996, 37, 8355.
6. Wagner, R. W.; Matteucci, M. D.; Lewis, J. G.; Gutierrez, A. J.; Molds, C.; Froehler, B. C. Science 1993, 260, 1510.
7. Ienaga, K.; Pfleiderer, W. Chem. Ber. 1977, 110, 3449.
8. (a) Maurinsch, Y.; Pfleiderer, W. Nucleosides Nucleotides 1996, 15, 431.
9. (b) Rosier, A.; Pfleiderer, W. Helv. Chim. Acta 1997, 80, 1869.
10. (a) Dudycz, L. W.; Wright, G. E. Nucleosides Nucleotides 1984, 3, 33.
11. (b) Wright, G. E.; Dudycz, L. W. J. Med. Chem. 1985, 27, 175.
12. (c) Garner, P.; Ramakanth, S. J. Org. Chem. 1988, 53, 1294.
13. For solutions of the regiochemical problem of guanine glycosylation, see: (a) Robins, M. J.; Zou, R.; Guo, Z.; Wnuk. S. F. J. Org. Chem. 1996, 61. 9207.
14. (b) Jenny. T. F.; Benner, S. A. Tetrahedron Lett. 1992, 33, 6619.
15. (a) Vorbrüggen H. F.; Ruh-Pohlenz, C. Org. React. 2000, 55, 1.
16. (b) Vorbrüggen H. Acc. Chem. Res. 1995, 28, 509.
17. (c) Vorbruggen, H. Acta Biochim. Pol. 1996, 43, 25.
18. Ewers, U.; Günther, H.; Jaenicke, L. Chem. Ber. 1974, 107, 876.
19. (a) Park, M.; Rizzo, C. J. J. Org. Chem. 1996, 61, 6092.
20. (b) Wang, Z.; Rizzo, C. J. Tetrahedron Lett. 1997, 38, 8177.
21. (c) Prudhomme, D. R.; Wang, Z.; Rizzo, C. J. J. Org. Chem. 1997, 62, 8257.
22. Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059.
23. Markiewicz, W. T. J. Chem. Res., Synop. 1979, 24.
24. Rasmussen, J. R.; Slinger, C. J.; Kordish, R. J.; Newman-Evans, D. D. J. Org. Chem. 1981, 46, 4843.
25. Barton, D. H. R.; Blundell, P.; Dorchak, J.; Jang, D. O.; Jaszberenyi, J. C. Tetrahedron 1991, 43, 8969.
26. (a) Marumoto, R.; Honjo, M. Chem. Pharm. Bull. 1974, 22, 128.
27. (b) David, S.; Auge, C. Carbohydr. Res. 1973, 28, 125.
28. (c) Pankiewicz, K. W.; Wantanabe, K. A. Chem. Pharm. Bull. 1987, 35, 4494.
29. (d) Shiragami, H.; Ineyama, T.; Uchida, Y.; Izawa, K. Nucleosides Nucleotides 1996, 15, 47.
30. (e) Holy, A. In Nucleic Acid Chemistry; Townsend, L. B., Tipson, R. S., Eds.; Wiley: New York, 1978; Vol. 1, pp 347-353.
31. (f) Rama Rao, A. V.; Gurjar, M. K.; Lalitha, S. V. S. J. Chem. Soc., Chem. Commun. 1994, 1255.