Friedel-Crafts and modified Vorbrüggen ribosylation. A short synthesis of aryl and heteroaryl-C-nucleosides

Tetrahedron Letters

Volumn 49, Issue 25, 2008, Pages 3967-3971

  Spadafora, Marie ^a   Mehiri, Mohamed ^a   Burger, Alain ^a   Benhida, Rachid ^a  

^a CNRS   (France)

Author keywords

C Nucleosides; Friedel Crafts ribosylation; Modified Vorbr ggen reaction

Indexed keywords

C NUCLEOSIDE; RIBOSE; TETRA O ACETYLRIBOSE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

TETRA;

EID: 43449130076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.105     Document Type: Article

References (35)

1. For the biological and clinical impact of tiazofurin and benzamide riboside see:. Grifantini M. Curr. Opin. Invest. Drugs 1 (2000) 257
2. Szekeres T., Sedlak J., and Novotny L. Curr. Med. Chem. 9 (2002) 759
3. Ratcliffe A.J. Curr. Opin. Drug Discov. Devel. 9 (2006) 595
4. Chen L., and Pankiewicz K.W. Curr. Opin. Drug Discov. Devel. 10 (2007) 403
5. For recent reviews on the chemistry and the biochemistry of C-glycoside analogues, see:. Wu Q., and Simons C. Synthesis (2004) 1533
6. Bililign T., Griffith B.R., and Thorson J.S. Nat. Prod. Rep. 22 (2005) 742
7. Lee D.Y.W., and He M.S. Curr. Top. Med. Chem. 5 (2005) 1333
8. Bililign T., Griffith B.R., and Thorson J.S. Nat. Prod. Rep. 22 (2005) 742
9. Kool E.T. Acc. Chem. Res. 35 (2002) 936
10. Ren R.X.F., Chaudhuri N.C., Paris P.L., Rummey S., and Kool E.T. J. Am. Chem. Soc. 118 (1996) 7671
11. Chaudhuri N.C., Reu R.X., and Kool E.T. Synlett (1997) 341
12. Hocek M., Pohl R., and Klepetarova B. Eur. J. Org. Chem. (2005) 4525
13. Gudmundsson K.S., Drach J.C., and Townsend L.B. J. Org. Chem. 62 (1997) 3453
14. Batoux N.E., Paradisi F., Engel P.C., and Migaud M.E. Tetrahedron 60 (2004) 6609
15. Guianvarc'h D., Fourrey J.-L., Tran Huu Dau M.-E., Guérineau V., and Benhida R. J. Org. Chem. 67 (2002) 3724
16. Singh I., and Seitz O. Org. Lett. 8 (2006) 4319
17. Harusawa S., Matsuda C., Araki L., and Kurihara T. Synthesis (2006) 793
18. For the synthesis of aryl C-glycosides via the Heck reaction, see:. Wellington K.W., and Benner S.A. Nucleosides, Nucleotides Nucleic acids (2005) 1309 review
19. Oda H., Hanami T., Iwashita T., Kojima M., Itoh M., and Hayashizaki Y. Tetrahedron 63 (2007) 12747
20. See, for example:. Hanessian S. Chem. Rev. 100 (2000) 4443
21. Kumazawa T., Onda K., Okuyama H., Matsuba S., Sato S., and Onodera J. Carbohydr. Res. 337 (2002) 1007
22. Li Y., Wei G., and Yu B. Carbohydr. Res. 341 (2006) 2717
23. Hainke S., Arndt S., and Seitz O. Org. Biomol. Chem. 3 (2005) 4233 and references therein (in 2′-deoxy series)
24. Guianvarc'h D., Fourrey J.-L., Sun J.-S., Maurisse R., and Benhida R. Bioorg. Med. Chem. 11 (2003) 2751
25. Guianvarc'h D., Fourrey J.-L., Maurisse R., Sun J.-S., and Benhida R. Org. Lett. 4 (2002) 4209
26. El Akri K., Bougrin K., Balzarini J., Faraj A., and Benhida R. Bioorg. Med. Chem. Lett. 17 (2007) 6656
27. +. Small amount of the α-anomer was also observed in these reactions (≤8%).
28. +, 597.21002; found, 597.20950.
29. Niedballa U., and Vorbrüggen H. J. Org. Chem. 41 (1976) 2084
30. Vorbrüggen H., Krolikiewicz K., and Bennua B. Chem. Ber. 114 (1981) 1234
31. For review see:. Vorbrüggen H., and Ruh-Polenz C. Org. React. 55 (2000) 1-630
32. +.
33. For reviews of arylsilanes in electrophilic aromatic substitutions, see:. Eaborn C. J. Organomet. Chem. 100 (1975) 43
34. Fleming I. In: Barton D.H.R., and Ollis W.D. (Eds). Comprehensive Organic Chemistry Vol. 3, Chapter 13 (1979), Pergamon, Oxford 613
35. + 341.13843; found, 341.13835.