Synthesis of C-5 substituted nucleosides via palladium-catalyzed coupling of dienes and amines

Tetrahedron

Volumn 61, Issue 48, 2005, Pages 11427-11439

  Larock, Richard C ^a   Wang, Yao ^a   Dong, Xiaoyang ^a   Yao, Tuanli ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Coupling; Dienes; Nucleosides

Indexed keywords

ALKADIENE; AMINE; HYDROXYL GROUP; LEWIS ACID; PALLADIUM; PYRIMIDINE NUCLEOSIDE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 27544459839     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.065     Document Type: Article

References (37)

1. G.P. Connolly, and J.A. Duley TiPS 20 1999 218
2. R. Kumar Bioorg. Med. Chem. Lett. 12 2002 275
3. J. Neyts, E. Verbeken, and E. De Clercq Antimicrob. Agents Chemother. 46 2002 2842
4. M.L. Bryant Nucleosides Nucleotides 20 2001 597
5. S. Blewett, C. McGuigan, H. Barucki, G. Andrei, R. Snoeck, E. De Clercq, and J. Balzarini Nucleosides Nucleotides 20 2001 1063
6. O.M. Ashour, F.N.M. Naguib, N.M. Goudgaon, R.F. Schinazi, and M.H. el Kouni Biochem. Pharmacol. 60 2000 687
7. E.J. McIntee, and C.R. Wagner Bioorg. Med. Chem. Lett. 11 2001 2803
8. T.I. Kalman, Z. Nie, and A. Kamat Nucleosides Nucleotides 20 2001 869
9. C. Wojczewski, K. Stolze, and J.W. Engels Synlett 10 1999 1667
10. M.E. Hawkins Cell Biochem. Biophys. 34 2001 257
11. K. Nakatani, T. Yoshida, and I. Saito J. Am. Chem. Soc. 124 2002 2118
12. S. Bellon, D. Gasparutto, A. Romieu, and J. Cadet Nucleosides Nucleotides 20 2001 967
13. D.J. Hurley, S.E. Seaman, J.C. Mazura, and Y. Tor Org. Lett. 4 2002 2305
14. L.J. Brown, J.P. May, and T. Brown Tetrahedron Lett. 42 2001 2587
15. H. Ozaki, M. Mine, Y. Ogawa, and H. Sawai Bioorg. Chem. 29 2001 187
16. J.L. Ruth, and D.E. Bergstrom J. Org. Chem. 43 1978 2870
17. D.E. Bergstrom, and M.K. Ogawa J. Am. Chem. Soc. 100 1978 8106
18. A.S. Jones, G. Verhelst, and R.T. Walker Tetrahedron Lett. 1979 4415
19. A. Ciurea, C. Fossey, S. Benzaria, D. Gavriliu, Z. Delbederi, B. Lelong, D. Laduree, A.M. Aubertin, and A. Kirn Nucleosides Nucleotides 20 2001 1655
20. N. Amann, and H.A. Wagenknecht Synlett 2002 687
21. A.J. Gutierrez, T.J. Terhorst, M.D. Matteucci, and B.C. Froehler J. Am. Chem. Soc. 116 1994 5540
22. R.C. Larock, and Y. Wang Tetrahedron Lett. 43 2002 21
23. R.C. Larock, Y. Wang, Y. Lu, and C.E. Russell J. Org. Chem. 59 1994 8107
24. R.C. Larock, Y.-D. Lu, A.C. Bain, and C.E. Russell J. Org. Chem. 56 1991 4589
25. E. De Clercq, and R.T. Walker G.P. Ellis G.B. West Progress in Medicinal Chemistry Vol. 23 1986 Elsevier Amsterdam 187
26. B.A. Patel, L.-C. Kao, N.A. Cortese, J.V. Minkiewicz, and R.F. Heck J. Org. Chem. 44 1979 918
27. J.M. O'Connor, B.J. Stallman, W.G. Clark, A.Y.L. Su, R.E. Spada, T.M. Stevenson, and H.A. Dieck J. Org. Chem. 48 1983 807
28. I. Shimizu, and J. Tsuji Chem. Lett. 1984 233
29. I.W. Davies, I.C. Scopes, and T. Gallagher Synlett 1993 85
30. R.C. Larock, N.G. Berrios-Pena, and C.A. Fried J. Org. Chem. 56 1991 2615
31. R.D. Walkup, L. Guan, M.D. Mosher, S.W. Kim, and Y.S. Kim Synlett 1993 88
32. V. Gauthier, B. Cazes, and J. Gore Tetrahedron Lett. 32 1991 915
33. M. Ahmar, B. Cazes, and J. Gore Tetrahedron Lett. 26 1985 3795
34. M. Ahmar, B. Cazes, and J. Gore Tetrahedron Lett 43 1987 3453
35. Cacchi, S. Personal communication.
36. J.-i. Asakura, and M.J. Robins J. Org. Chem. 55 1990 4928
37. P.K. Chang, and A.D. Welch J. Med. Chem. 6 1963 428