Dinucleotides of 4′-C-vinyl- and 5′-C-allylthymidine as substrates for ring-closing metathesis reactions

Tetrahedron Letters

Volumn 44, Issue 34, 2003, Pages 6475-6478

  Kirchhoff, Claus ^a   Nielsen, Poul ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

4' C VINYLTHYMIDINE; 5' C ALLYLTHYMIDINE; DIMER; DINUCLEOTIDE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; EVALUATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS;

HOMO;

EID: 0043199417     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01584-3     Document Type: Article

References (33)

1. Kool E.T. Chem. Rev. 97:1997;1473.
2. Leumann C.J. Bioorg. Med. Chem. 10:2002;841.
3. Meldgaard M., Wengel J. J. Chem. Soc., Perkin Trans. 1. 2000;3539.
4. Belmont P., Constant J.-F., Demeunynck M. Chem. Soc. Rev. 30:2001;70.
5. Sekine M., Kurasawa O., Shohda K., Seio K., Wada T. Eur. J. Org. Chem. 2001;1989.
6. Sekine M., Kurasawa O., Shohda K., Seio K., Wada T. J. Org. Chem. 65:2000;6515.
7. Le Clézio I., Escudier J.-M., Vigroux A. Org. Lett. 5:2003;161.
8. Seio K., Wada T., Sekine M. Helv. Chim. Acta. 83:2000;162.
9. For a review, see: Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012.
10. Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18.
11. Sørensen A.M., Nielsen P. Org. Lett. 2:2000;4217.
12. Sørensen A.M., Nielsen K.E., Vogg B., Jacobsen J.P., Nielsen P. Tetrahedron. 57:2001;10191.
13. Børsting P., Sørensen A.M., Nielsen P. Synthesis. 2002;797.
14. Børsting P., Nielsen P. Chem. Commun. 2002;2140.
15. Preparation of 4′-C-vinylthymidine has been accomplished from a radical-cyclisation reaction with a 3′-O-vinylsilyl tether: (a) Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385; (b) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153.
16. Preparation of 4′-C-vinylthymidine has been accomplished from a radical-cyclisation reaction with a 3′-O-vinylsilyl tether: (a) Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385; (b) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153.
17. Recently, a preparation similar to ours of the 4′-C-vinylthymidine derivative 5 was presented: (a) Summerer, D.; Marx, A. Angew. Chem., Int. Ed. 2001, 40, 3693; (b) Detmer, I.; Summerer, D.; Marx, A. Eur. J. Org. Chem. 2003, 1837.
18. Recently, a preparation similar to ours of the 4′-C-vinylthymidine derivative 5 was presented: (a) Summerer, D.; Marx, A. Angew. Chem., Int. Ed. 2001, 40, 3693; (b) Detmer, I.; Summerer, D.; Marx, A. Eur. J. Org. Chem. 2003, 1837.
19. Recently, 3′-O-allyl-5′-O-TBDPS-4′-C-vinylthymidine has been prepared and used as a substrate for an RCM-reaction affording a 3′-O,4′-C-bicyclic nucleoside derivative: Montembault, M.; Bourgougnon, N.; Lebreton, J. Tetrahedron Lett. 2002, 43, 8091.
20. Banuls V., Escudier J.-M. Tetrahedron. 55:1999;5831.
21. O-Yang C., Wu H.Y., Fraser-Smith E.B., Walker K.A.M. Tetrahedron Lett. 33:1992;37.
22. Thrane H., Fensholdt J., Regner M., Wengel J. Tetrahedron. 37:1995;10389.
23. O-Yang C., Kurz W., Eugui E.M., McRoberts M.J., Verheyden J.P.H., Kurz L.J., Walker K.A.M. Tetrahedron Lett. 33:1992;41.
24. Compound 2 has been obtained before by different protecting group manipulations: Wang G., Seifert W.E. Tetrahedron Lett. 37:1996;6515.
25. Marx A., Erdmann P., Senn M., Körner S., Jungo T., Petretta M., Imwinkelried P., Dussy A., Kulicke K.J., Macko L., Zehnder M., Giese B. Helv. Chim. Acta. 79:1996;1980.
26. A different Wittig olefination performed after oxidation of 1 and 5′-O-tritylation has been reported: Maag H., Schmidt B., Rose S.J. Tetrahedron Lett. 35:1994;6449.
27. Bou V., Vilarrasa J. Tetrahedron Lett. 31:1990;567.
28. Higashibayashi S., Shinko K., Ishizu T., Hashimoto K., Shirahama H., Nakata M. Synlett. 9:2000;1306.
29. The unprotected 4′-C-vinylthymidine was fully characterized and the data were in accordance with data given for the compound obtained by a different strategy; Ref. 13a.
30. Vargeese C., Carter J., Yegge J., Krivjansky S., Settle A., Kropp E., Peterson K., Pieken W. Nucleic Acid Res. 26:1998;1046.
31. Caruthers M.H. Acc. Chem. Res. 55:1991;5831.
32. +] (found/calcd): 9 (1026.3906, 1026.3876); 14 (1044.3672, 1044.3587); 15 (1016.3289, 1016.3274); 16 (1164.4368, 1164.4346); 17 (1136.4033, 1135.4067).
33. Wang, G.; Middleton, P. J. Tetrahedron Lett. 1996, 37, 2739 and Nucleosides Nucleotides 1998, 17, 1033.