Synthesis of 4′-C, 3′-O bicyclic thymidine analogues using ring closure metathesis

Tetrahedron Letters

Volumn 43, Issue 45, 2002, Pages 8091-8094

  Montembault, Mickael ^a   Bourgougnon, Nathalie ^b   Lebreton, Jacques ^a  

^a Centre National de la Recherche Scientifique   (France)

^b UNIVERSITÉ DE BRETAGNE SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; THYMIDINE DERIVATIVE;

ARTICLE; CATALYST; CONTROLLED STUDY; DRUG ACTIVITY; DRUG OXIDATION; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; NONHUMAN; RING CLOSING METATHESIS; VIRUS INHIBITION;

EID: 0037020648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01926-3     Document Type: Article

References (36)

1. Mitsuya H., Weinhold K.J., Furman P.A., St. Clair M.H., Nusinoff-Lehrman S., Gallo R.C., Bolognesi D.P., Barry D.W., Broder S. Proc. Natl. Acad. Sci. USA. 82:1985;7096-7100.
2. Yarchoan R., Broder S. Pharmacol. Ther. 40:1989;329-348.
3. DeClerq E. J. Med. Chem. 38:1995;2491-2517. and references cited therein.
4. Tan X., Chu C.K., Boudinot F.D. Adv. Drug Deliv. Rev. 39:1999;117-151. and references cited therein.
5. Bamford M.J., Coe P.L., Walker R.T. J. Med. Chem. 33:1990;2488-2494.
6. Gurjar M.K., Maheshwar K. J. Org. Chem. 66:2001;7552-7554.
7. Crimmins M.A. Tetrahedron. 54:1998;9229-9272.
8. Bisacchi G.S., Chao S.T., Bachard C., Daris J.P., Inaimo S., Jacobs G.A., Kocy O., Lapointe P., Martel A., Merchant Z., Slusarchyk W.A., Sundeen J.E., Young M.G., Colonno R., Zahler R. Bioorg. Med. Chem. Lett. 7:1997;127-132.
9. Agrofoglio L.A., Challand S.R. Acyclic, Carbocyclic and L-Nucleosides. 1998;174-284 Kluwer Academic Published, Dordrecht.
10. Lin T.S., Luo M.Z., Liu M.C., Pai S.B., Dutschman G.E., Cheng Y.C. J. Med. Chem. 37:1994;798-803.
11. Pineda Molas M., Matheu M.I., Castillón S., Isac-García J., Hernández-Mateo F., Calvo-Flores F.G., Santoyo-González F. Tetrahedron. 55:1999;14649-14664.
12. Chao Q., Zhang J., Pickering L., Jahnke T.S., Nair V. Tetrahedron. 54:1998;3113-3124.
13. Björsne M., Szabò T., Samuelsson B., Classon B. Bioorg. Med. Chem. Lett. 3:1995;397-402.
14. Many 2′-O, 4′-C- and 3′-O, 4′-C-methylenenucleosides have been synthesized and incorporated into antisense and antigene oligonucleotides, for reviews concerning this point, see: (a) Leumann, C. J. Bioorg. Med. Chem. 2002, 10, 841-854; (b) Meldgaard, M.; Wengel, J. J. Chem. Soc., Perkin Trans. 1 2000, 3539-3554.
15. Many 2′-O, 4′-C- and 3′-O, 4′-C-methylenenucleosides have been synthesized and incorporated into antisense and antigene oligonucleotides, for reviews concerning this point, see: (a) Leumann, C. J. Bioorg. Med. Chem. 2002, 10, 841-854; (b) Meldgaard, M.; Wengel, J. J. Chem. Soc., Perkin Trans. 1 2000, 3539-3554.
16. For examples of 3′-O, 4′-C-methylenethymidines, see: Yang, C. O.; Kurz, W.; Eugui, E. M.; McRoberts, M. J.; Verheyden, J. P. H.; Kurz, L. J.; Walker, A. M. Tetrahedron Lett. 1992, 33, 33-41. For examples of 3′-O, 4′-C-ethylenethymidines, see: Sigimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385-388.
17. For examples of 3′-O, 4′-C-methylenethymidines, see: Yang, C. O.; Kurz, W.; Eugui, E. M.; McRoberts, M. J.; Verheyden, J. P. H.; Kurz, L. J.; Walker, A. M. Tetrahedron Lett. 1992, 33, 33-41. For examples of 3′-O, 4′-C-ethylenethymidines, see: Sigimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385-388.
18. For general reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, (2) 371-388; (c) Furstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012-3043 and references cited therein.
19. For general reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, (2) 371-388; (c) Furstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012-3043 and references cited therein.
20. For general reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, (2) 371-388; (c) Furstner, A. Angew. Chem., Int. Ed. Engl. 2000, 39, 3012-3043 and references cited therein.
21. For articles concerning the use of the metathesis reaction in the nucleoside field, see: (a) Borsting, P.; Sorensen, A. M.; Nielsen, P.; Hoffmann, R. W. Synthesis 2002, 797-801; (b) Ewing, D., Glaçon, V.; Mackenzie, G.; Postel, D.; Len, C. Tetrahedron Lett. 2002, 43, 3503-3505; (c) Lera, M.; Hayes, C. J. Org. Lett. 2001, 3, 2765-2768; (d) Batoux, N.; Benhaddon-Zerouki, R.; Bressolier, P.; Granet, R.; Laumont, G.; Aubertin, A.-M.; Krausz, P. Tetrahedron Lett. 2001, 42, 1491-1493.
22. For articles concerning the use of the metathesis reaction in the nucleoside field, see: (a) Borsting, P.; Sorensen, A. M.; Nielsen, P.; Hoffmann, R. W. Synthesis 2002, 797-801; (b) Ewing, D., Glaçon, V.; Mackenzie, G.; Postel, D.; Len, C. Tetrahedron Lett. 2002, 43, 3503-3505; (c) Lera, M.; Hayes, C. J. Org. Lett. 2001, 3, 2765-2768; (d) Batoux, N.; Benhaddon-Zerouki, R.; Bressolier, P.; Granet, R.; Laumont, G.; Aubertin, A.-M.; Krausz, P. Tetrahedron Lett. 2001, 42, 1491-1493.
23. For articles concerning the use of the metathesis reaction in the nucleoside field, see: (a) Borsting, P.; Sorensen, A. M.; Nielsen, P.; Hoffmann, R. W. Synthesis 2002, 797-801; (b) Ewing, D., Glaçon, V.; Mackenzie, G.; Postel, D.; Len, C. Tetrahedron Lett. 2002, 43, 3503-3505; (c) Lera, M.; Hayes, C. J. Org. Lett. 2001, 3, 2765-2768; (d) Batoux, N.; Benhaddon-Zerouki, R.; Bressolier, P.; Granet, R.; Laumont, G.; Aubertin, A.-M.; Krausz, P. Tetrahedron Lett. 2001, 42, 1491-1493.
24. For articles concerning the use of the metathesis reaction in the nucleoside field, see: (a) Borsting, P.; Sorensen, A. M.; Nielsen, P.; Hoffmann, R. W. Synthesis 2002, 797-801; (b) Ewing, D., Glaçon, V.; Mackenzie, G.; Postel, D.; Len, C. Tetrahedron Lett. 2002, 43, 3503-3505; (c) Lera, M.; Hayes, C. J. Org. Lett. 2001, 3, 2765-2768; (d) Batoux, N.; Benhaddon-Zerouki, R.; Bressolier, P.; Granet, R.; Laumont, G.; Aubertin, A.-M.; Krausz, P. Tetrahedron Lett. 2001, 42, 1491-1493.
25. Nomura M., Shuto S., Tanaka M., Sasaki T., Mori S., Shigeta S., Matsuda A. J. Med. Chem. 42:1999;32901-32908.
26. 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;1980-1994.
27. Purification on silica gel column led to the desired compound in 80% yield accompanied by the corresponding bis-allyl-2-N-, 3′-O-derivative in 10% yield and unreacted starting material in 10% yield.
28. Chattopadhyaya et al. reported the preparation of a dozen 2′- or 3′-O-allyl and propargyl ether uracil derivatives under ultrasonic conditions, see: Wu, J.-C.; Xi, Z.; Gioeli, C.; Chattopadhyaya, J. Tetrahedron 1991, 47, 2237-2254. Under these conditions, the formation of the 2-N-alkylated derivative seems to be minimized.
29. It should be mentioned that another elegant access to 4′-α-vinyl nucleoside analogues using radical chemistry has been reported, see: Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157 and references cited therein.
30. The best overall yields in this sequence 6 to 4 were obtained when the aldehyde intermediate was purified on silica gel chromatography.
31. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4156-4158.
32. Meyer S.D., Schreiber S.L. J. Org. Chem. 59:1994;7549-7552.
33. Summerer D., Marx A. Angew. Chem., Int. Ed. Engl. 40:2001;3693-3695.
34. + 461.1533, found 461.1539.
35. + 280.1059, found 280.1060.
36. + 282.1216, found 282.1218.