Alkynyl-2-deoxy-d-riboses, a cornucopia for the generation of families of C-nucleosides

Tetrahedron

Volumn 66, Issue 47, 2010, Pages 9242-9251

  Adamo, Mauro F A ^a   Pergoli, Roberto ^a   Moccia, Maria ^a  

^a ROYAL COLLEGE OF SURGEONS IN IRELAND   (Ireland)

Author keywords

1 Alkynylsugars; Anti microbial; C Nucleosides; Diversity oriented synthesis

Indexed keywords

2 DEOXYRIBOSE; ALCOHOL DERIVATIVE; ALKYNE; NUCLEOSIDE ANALOG;

ALKYLATION; ARTICLE; CYCLOADDITION; DEPROTECTION REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION OPTIMIZATION;

EID: 78049256263     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.046     Document Type: Article

References (45)

1. K. Mizuno, M. Tsujino, M. Takada, K. Hayashi, K. Atsumi, K. Asano, and T.T. Matsuda J. Antibiot. 27 1974 775
2. H. Amenmiya, and H.I. Itoh A.W. Thompson, T.E. Starzt, Immunosuppressive Drugs: Developments in Anti-rejection Therapy 1993 Edward Arnord London 161 176
3. S.A. Giruber Immunol. Rev. 129 1992 5
4. L.A. Turka, J. Dayton, G. Sinclair, C.B. Thomson, and B.S. Mitchell J. Clin. Invest. 87 1991 940
5. S.H. Krawczyc, M.R. Nassiri, L.S. Kucera, E.R. Kern, R.G. Ptak, L.L. Wotring, J.C. Drach, and L.B. Townsend J. Med. Chem. 38 1995 4106
6. Y. Kato, N. Fusetani, S. Matsunaga, and K. Hashimoto Tetrahedron Lett. 29 1985 3483
7. J.G. Buchanan, and R.H. Wightman Top. Antibiot. Chem. 6 1982 229
8. A.M. Mubarak, and D.M. Brown Tetrahedron Lett. 22 1981 683
9. M.A.E. Shaban, and A.Z. Nasr Adv. Heterocycl. Chem. 68 1997 223
10. M.A.E. Sallam, F.F. Luis, and J.M. Cassady Nucleosides Nucleotides 17 1998 769
11. M.L. Sethi W.O. Foye, T.L. Lemke, D.A. Williams, Principles of Medicinal Chemistry 5th ed. 2002 Lippincott, Williams and Wilkins Philadelphia, PA 952
12. For reviews on the chemistry and biochemistry of C-nucleoside analogues, see:
13. U. Hacksell, and G.D. Daves Jr. Prog. Med. Chem. 22 1985 1
14. M.H.D. Postema Tetrahedron 48 1992 8545
15. K.A. Watanabe L.B. Townsend, Chemistry of Nucleosides and Nucleotides Vol. 3 1994 Plenum New York, NY 421
16. C. Jaramillo, and S. Knapp Synthesis 1994 1
17. H. Togo, W. He, Y. Waki, and M. Yokoyama Synlett 1998 700
18. E.T. Kool Annu. Rev. Biochem. 71 2002 191
19. Q. Wu, and C. Simons Synthesis 10 2004 1533
20. G.H. Elgemeie, W.A. Zaghary, K.M. Amin, and T.M. Nasr Nucleosides Nucleotides Nucleic Acids 24 2005 1227
21. K.W. Wellington, and S.A. Benner Nucleosides Nucleotides Nucleic Acids 25 2006 1309
22. M.F.A. Adamo, and R. Pergoli Curr. Org. Chem. 12 2008 1544
23. J.S. Tambasky, M. Hocek, and P. Kocovsky Chem. Rev. 109 2009 6729
24. M.F.A. Adamo, and R. Pergoli Org. Lett. 9 2007 4443
25. T. Masayoshi, T. Morikawa, H. Abe, and M. Inouye Org. Lett. 5 2003 625
26. Y. Doi, J. Chiba, T. Morikawa, and M. Inouye J. Am. Chem. Soc. 130 2008 8762
27. H. Hattori, E. Nozawa, T. Iino, Y. Yoshimura, S. Shuto, Y. Shimamoto, M. Nomura, M. Fukushima, M. Tanaka, T. Sasaki, and A. Matzuda J. Med. Chem. 41 1998 2892
28. H. Ohrui, S. Kohgo, K. Kitano, S. Sakata, E. Kodama, K. Yoshimura, M. Matsuoka, S. Shigeta, and H. Mitzuya J. Med. Chem. 43 2000 4516
29. M.E. Jung, and M.A. Lyster J. Org. Chem. 42 1977 3761
30. B. ElAmin, G.M. Anantharamaiah, G.P. Royer, and G.E. Means J. Org. Chem. 44 1979 3442
31. T. Bieg, and W. Szeja Synthesis 1985 76
32. J.P. Kutney, N. Abdurahman, C. Gletsos, P. LeQuesne, E. Piers, and I. Vlattas J. Am. Chem. Soc. 92 1970 1727
33. A.S. Hay J. Org. Chem. 27 1962 3320
34. R. Rossi, A. Carpita, and C. Bigelli Tetrahedron Lett. 26 1985 523
35. Q. Liu, and D.J. Burton Tetrahedron Lett. 38 1997 4371
36. A. Elangovan, Y.H. Wang, and T.I. Ho Org. Lett. 5 2003 1841
37. N. Joubert, R. Pohl, B. Klepetářová, and M. Hocek J. Org. Chem. 72 2007 6797
38. During preparation of this manuscript an alternative procedure for the efficient coupling of tolyl protected 1-alkynyl-2-deoxy-d-riboses and iodoaromatic species was reported, see T. Bobula, M. Hocek, and M. Kotora Tetrahedron 66 2010 530
39. K.I. Itoh, and C.A. Horiuchi Tetrahedron 60 2004 1671
40. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
41. B.Y. Lee, S.R. Park, H.B. Jeon, and K.S. Kim Tetrahedron Lett. 47 2006 5105
42. T.R. Chan, R. Hilgraf, K.B. Sharpless, and V.V. Fokin Org. Lett. 6 2004 2853
43. P. Novák, R. Pohl, M. Kotora, and M. Hocek Org. Lett. 8 2006 2051
44. N.E. Shore Org. React. 41 1991 1
45. W.J. Kerr, M. McLaughlin, P.L. Pauson, and S.M. Robertson J. Organomet. Chem. 630 2001 104