Synthesis of adenosine-based fluorosides containing a novel heterocyclic ring system

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6745-6748

  O'Mahony, Gavin ^a   Ehrman, Eleonor ^a   Grøtli, Morten ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Cross coupling; Cycloaddition; Nucleosides; Palladium

Indexed keywords

ADENOSINE DERIVATIVE; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND; PURINE DERIVATIVE;

ARTICLE; CYCLOADDITION; DEPROTECTION REACTION; DRUG SYNTHESIS; SONOGASHIRA REACTION; SUBSTITUTION REACTION;

EID: 23944468997     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.115     Document Type: Article

References (25)

1. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
2. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128 1137
3. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
4. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
5. R. Huisgen Pure Appl. Chem. 61 1989 613 628
6. R. Huisgen, G. Szeimies, and L. Möbius Chem. Ber. 100 1967 2494 2507
7. W. Lwowski A. Padwa 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 John Wiley New York 559 651
8. C.-K. Sha, and A. Mohanakrishnan A. Padwa W.H. Pearson Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products 2002 John Wiley New York 623 679
9. For 1,3-dipolar cycloadditions employing azides in the preparation of carbohydrate derivatives: A.E. Koumbis, and J.K. Gallos Curr. Org. Chem. 7 2003 771 797
10. S. Hotha, R.I. Anegundi, and A.A. Natu Tetrahedron Lett. 46 2005 4585 4588
11. M. Ikehara, and M. Kaneko Tetrahedron 26 1970 4251 4259
12. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467 4470
13. K. Sonogashira B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon Press New York 521
14. For Sonogashira cross-coupling reactions involving nucleosides see C. Lambertucci, S. Constanzi, S. Vittori, R. Volpini, and G. Cristalli Nucleosides Nucleotides 20 2001 1153 1157
15. W. Flasche, C. Cismas, A. Herrmann, and J. Liebscher Synthesis 2004 2335 2341
16. J. Gao, C. Strässler, D. Tahmassebi, and E.T. Kool J. Am. Chem. Soc. 124 2002 11590 11591
17. T. Maruyama, S. Kozai, T. Manabe, Y. Yazima, Y. Satoh, and H. Takaku Nucleosides Nucleotides 18 1999 2433 2442
18. M.J. Robins, S.D. Hawrelak, A.E. Hernández, and S.W. Wnuk Nucleosides Nucleotides 11 1992 821 834
19. W.H. Melhuish J. Phys. Chem. 65 1961 229 235
20. W. Zhang, and M.J. Robins Tetrahedron Lett. 33 1992 1177 1180
21. 3: C, 45.6; H, 3.8; N, 35.4. Found: C, 45.4; H, 3.9; N, 35.3.
22. -1, KBr disk) 3386, 2945, 2868, 2365, 1640, 1583, 1466, 1420, 1367, 1332, 1293, 1249, 1213, 1146, 1037, 952, 885, 777, 700, 602, 453.
23. G. Alonso, M.T. Garcia-López, G. García-Munõz, R. Madroñero, and R. Rico J. Heterocycl. Chem. 7 1970 1272 1296
24. 2 requires 686.204).
25. A. Matsuda, M. Shinozaki, T. Yamaguchi, H. Homma, R. Nomoto, T. Miyasaka, Y. Watanabe, and T. Abiru J. Med. Chem. 35 1992 241 252