A new alkylation-elimination method for synthesis of antiviral fluoromethylenecyclopropane analogues of nucleosides

Tetrahedron

Volumn 61, Issue 30, 2005, Pages 7112-7116

  Zhou, Shaoman ^a   Zemlicka, Jiri ^a  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Alkylation elimination; Fluoromethylenecyclopropane nucleoside analogues; Methylenecyclopropanes

Indexed keywords

CYCLOPROPANE DERIVATIVE; GUANINE DERIVATIVE; NUCLEOSIDE ANALOG;

ALKYLATION; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DEACETYLATION; DRUG ACETYLATION; DRUG SYNTHESIS; ELIMINATION REACTION; FLUORINATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

HUMAN ECHOVIRUS 1;

EID: 20544439584     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.054     Document Type: Article

References (22)

1. J. Zemlicka C.K. Chu Recent Advances in Nucleosides: Chemistry and Chemotherapy 2002 Elsevier Amsterdam, The Netherlands 327 357
2. J. Zemlicka, and X. Chen Methylenecyclopropane Analogues of Nucleosides as Antiviral Agents R.F. Schinazi D.C. Liotta Frontiers in Nucleosides and Nucleic Acids 2004 IHL Tucker, GA 267 307
3. S. Zhou, E.R. Kern, E. Gullen, Y.-C. Cheng, J.C. Drach, S. Matsumi, H. Mitsuya, and J. Zemlicka J. Med. Chem. 47 2004 6964 6972
4. Y.-L. Qiu, M.B. Ksebati, R.G. Ptak, B.Y. Fan, J.M. Breitenbach, J.-S. Lin, Y.-C. Cheng, E.R. Kern, J.C. Drach, and J. Zemlicka J. Med. Chem. 41 1998 10 23
5. Y.-L. Qiu, R.G. Ptak, J.M. Breitenbach, J.-S. Lin, Y.-C. Cheng, E.R. Kern, J.C. Drach, and J. Zemlicka Antiviral Chem. Chemother. 9 1998 341 352
6. X. Chen, E.R. Kern, J.C. Drach, E. Gullen, Y.-C. Cheng, and J. Zemlicka J. Med. Chem. 46 2003 1531 1537
7. Y.-L. Qiu, and J. Zemlicka Synthesis 1998 1447 1452
8. X. Chen, and J. Zemlicka J. Org. Chem. 67 2002 286 289
9. S. Zhou, J.M. Breitenbach, K.Z. Borysko, J.C. Drach, E.R. Kern, E. Gullen, Y.-C. Cheng, and J. Zemlicka J. Med. Chem. 47 2004 566 575
10. H.-P. Guan, Y.-L. Qiu, M.B. Ksebati, E.R. Kern, and J. Zemlicka Tetrahedron 58 2002 6047 6059
11. R. Wang, M.B. Ksebati, T.H. Corbett, E.R. Kern, J.C. Drach, and J. Zemlicka J. Med. Chem. 44 2001 4019 4022
12. H.-P. Guan, M.B. Ksebati, Y.-C. Cheng, J.C. Drach, E.R. Kern, and J. Zemlicka J. Org. Chem. 65 2000 1280 1290
13. H.-P. Guan, M.B. Ksebati, E.R. Kern, and J. Zemlicka J. Org. Chem. 65 2000 5177 5184
14. R. Wang, E.R. Kern, and J. Zemlicka Antiviral Chem. Chemother. 13 2002 251 262
15. T.G. Back Electrophilic Selenium Reactions D. Liotta Organoselenium Chemistry 1987 Wiley New York 1 125 loc. cit. p 59
16. P.L. Beaulieu, and R. Dezile T.G. Back Organoselenium Chemistry 1999 Oxford University Press New York 35 66
17. D. Liotta, G. Zima, and M. Saindane J. Org. Chem. 47 1982 1258 1267
18. J.A. Tunge, and S.R. Mellegard Org. Lett. 6 2004 1205 1207
19. T. Hori, and K.B. Sharpless J. Org. Chem. 44 1979 4208 4210
20. C. Muller, F. Stier, and P. Weyerstahl Chem. Ber. 110 1977 124 137
21. K.L. Williamson, Y.-F. Li, F.H. Hall, and S. Swager J. Am. Chem. Soc. 88 1966 5678 5680
22. 3 in fluorination of esters 2.