Diastereoselective and regioselective synthesis of conformationally restricted thio-dioxa- and oxo-oxathiaphosphorinane dinucleotides featuring noncanonical α/β torsion angle combinations (α,β-CNAs)

European Journal of Organic Chemistry

Volumn , Issue 12, 2007, Pages 1935-1941

  Le Clézio, Ingrid ^a   Vigroux, Alain ^a   Escudier, Jean Marc ^a  

^a CNRS   (France)

Author keywords

Constrained molecules; Cyclisation; Nucleic acids; Phosphorothioate; Regioselectivity

Indexed keywords

EID: 34250676157     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601030     Document Type: Article

References (28)

1. P. Herdewijn, Liebigs Ann. 1996, 1337-1348.
2. P. Herdewijn, Biochim. Biophys. Acta 1999, 1489, 167-179.
3. M. Meldgaard, J. Wengel, J. Chem. Soc., Perkin Trans. 1 2000, 3539-3554.
4. C. J. Leumann, Bioorg. Med. Chem. 2002, 10, 841-854.
5. a) K. Seio, T. Wada, K. Sakamoto, S. Yokoyama, M. Sekine, J. Org. Chem. 1998, 63, 1429-1443;
6. b) K. Seio, T. Wada, M. Sekine, Helv. Chim. Acta 2000, 83, 162-180;
7. c) M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada, J. Org. Chem. 2000, 65, 3571-3578;
8. d) M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada, J. Org. Chem. 2000, 65, 6515-6524;
9. e) M. Sekine, O. Kurasawa, K. Shohda, K. Seio, T. Wada, Eur. J. Org. Chem. 2001, 1989-1999.
10. a) A. M. Sørensen, P. Nielsen, Org. Lett. 2000, 2, 4217-4219;
11. b) A. M. Sørensen, K. E. Nielsen, B. Vogg, J. P. Jacobsen, P. Nielsen, Tetrahedron 2001, 57, 10191-10201;
12. c) P. Børsting, P. Nielsen, Chem. Commun. 2002, 2140-2141;
13. d) C. Kirchhoff, P. Nielsen, Tetrahedron Lett. 2003, 44, 6475-6478;
14. e) P. Børsting, M. Freitag, P. Nielsen, Tetrahedron 2004, 60, 10955-10966;
15. f) P. Børsting, K. E. Nielsen, P. Nielsen, Org. Biomol. Chem. 2005, 3, 2183-2190;
16. g) P. K. Sharma, B. H. Mikkelsen, M. S. Christensen, K. E. Nielsen, C. Kirchhoff, S. L. Pedersen, A. M. Sørensen, K. Østergaard, M. Petersen, P. Nielsen, Org. Biomol. Chem. 2006, 4, 2433-2445.
17. E. T. Kool, Chem. Rev. 1997, 97, 1473-1487.
18. I. Le Clezio, J.-M. Escudier, A. Vigroux, Org. Lett. 2003, 5, 161-164.
19. C. Dupouy, N. Iché-Tarrat, M.-P. Durrieu, F. Rodriguez, J.-M. Escudier, A. Vigroux, Angew. Chem. 2006, 118, 3705-3709;
20. Angew. Chem. Int. Ed. 2006, 45, 3623-3627.
21. I. Le Clezio, H. Gornitzka, J.-M. Escudier, A. Vigroux, J. Org. Chem. 2005, 70, 1620-1629.
22. C. Dupouy, I. Le Clezio, P. Lavedan, H. Gornitzka, J.-M. Escudier, A. Vigroux, Eur. J. Org. Chem. 2006, 24, 5515-5525.
23. M. H. Caruthers, Acc. Chem. Res. 1991, 24, 278-284.
24. R. G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533-3539.
25. D. G. Gorestein, 1984. Phosphorus P-31 NMR: Principles and Applications, Academic Press, Orlando, FL.
26. Heq,P < ca. 20 Hz, respectively. See: D. G. Gorenstein, R. Rowell, J. Findlay, J. Am. Chem. Soc. 1980, 102, 5077-5081.
27. 2(θ) - 6.1 cos (θ) + 1.6.
28. D. J. Wood, K. K. Ogilvie, F. E. Hruska, Can. J. Chem. 1975, 53, 2781-2790.