Stereocontrolled synthesis of α-2'-deoxyribonucleosides

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8177-8180

  Wang, Zhiwei ^a   Rizzo, Carmelo J ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RIBONUCLEOSIDE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030665608     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10251-9     Document Type: Article

References (29)

1. (a) Park, M.; Rizzo, C. J. J. Org. Chem. 1996, 61, 6092.
2. (b) for related work see: Huang, Z.; Schneider, K. C.; Benner, S. A. J. Org. Chem. 1991, 56, 3869.
3. For other examples of the PET deoxygenation in nucleoside chemistry see: (a) Barvian, M. R.; Barkley, R. M.; Greenberg, M. M. J. Am. Chem. Soc. 1995, 117, 4894.
4. (b) Barvian, M. R.; Greenberg, M. M. J. Org. Chem. 1993, 58, 6151.
5. (c) Barvian, M. R.; Greenberg, M. M. Tetrahedron Lett. 1992, 33, 6057.
6. Vorbrüggen H. Acc. Chem. Res. 1995, 28, 509.
7. Saito, I.; Ikehira, H.; Kasatani, R.; Watanabe, M.; Matsuura, T. J. Am. Chem. Soc. 1986, 108, 3115.
8. (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
9. (b) Wilson, L. W.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis 1995, 1465.
10. (c) Hunziker, J.; Leumann, C. Modern Synthetic Methods 1995: B. Ernst, C. Leumann, eds. VCH: Basel, 1995, pp. 333-417.
11. (a) Morvan, F.; Rayner, B.; Imbach, J.-L.; Chang, D.-K.; Lown, J. W. Nucleotides Nucleotides 1987, 6, 471.
12. (b) Debart, F.; Rayner, B.; Degols, G.; Imbach, J.-L. Nucleic Acids Res. 1992, 20, 1193.
13. (c) Gmeiner, W. H.; Rao, K. E.; Rayner, B.; Vasseur, J.-J.; Morvan, F.; Imbach, J.-L.; Lown, J. W. Biochemistry, 1990, 29, 10329.
14. (d) also see reference 5c and references therein.
15. (a) Morvan, F.; Rayner, B.; Imbach, J.-L.; Thenet, S.; Bertrand, J.-R.; Paoletti, J.; Malvy, C.; Paoletti, C. Nucleic Acids Res. 1987, 15, 3421.
16. (b) Cazenave, C.; Chevrier, M.; Thuong, N. T.; Helene, C. Nucleic Acids Res. 1987, 15, 10507.
17. (a) Yamaguchi, T.; Saneyoshi, M. Chem. Pharm. Bull. 1984, 32, 1441.
18. (b) Ward, D. I.; Jeffs, S. M.; Coe, P. L.; Walker, R. T. Tetrahedron Lett. 1993, 34, 6779.
19. Adams, A. D.; Petrie, C. R.; Meyer, R. B. Nucleic Acids Res. 1991, 19, 3647.
20. (a) Hughes, D. L. Organic Reactions 1992, 42, 335.
21. (b) Under different conditions, other authors found this Mitsunobu reaction to proceed with retention of configuration which we have also observed (Rubira, M. J.; Perez-Perez, M. J. unpublished results). We thanks Professor Perez-Perez for communicating these results to us prior to publication.
22. Ishido, Y.; Sakairi, N.; Sekiya, M.; Nakazaki, N. Carbohydrate Res. 1981, 97, 51.
23. Buu-Uoi, N. P.; Hoan, N. J. Org. Chem. 1951, 16, 1327.
24. Prudhomme, D. R.; Wang, Z.; Rizzo, C. J. J. Org. Chem. (in press)
25. 13C NMR.
26. (a) Dudycz, L. W.; Wright, G. E. Nucleosides Nucleotides 1984, 3, 33.
27. (b) Garner, P.; Ramakanth, S. J. Org. Chem. 1988, 53, 1294.
28. For recent solutions to the regioselectivity issue for guanine glycosylation see: (a) Robins, M. J.; Zou, R.; Guo, Z.; Wnuk, S. F. J. Org. Chem. 1996, 61, 9207.
29. (b) Mukaiyama, T.; Matsutani, T.; Shimomura, N. Chem. Lett. 1994, 2089.