Enantioselective syntheses of carbocyclic nucleosides 5′- homocarbovir, epi-4′-homocarbovir, and their cyclopropylamine analogs using facially selective Pd-mediated allylations

Tetrahedron

Volumn 67, Issue 5, 2011, Pages 825-829

  Tardibono Jr , Lawrence P ^a   Miller, Marvin J ^a   Balzarini, Jan ^b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

4' HOMOABACAVIR; 5' HOMOABACAVIR; CARBOCYCLIC NUCLEOSIDE; CARBOVIR; MALONIC ACID DERIVATIVE; PALLADIUM; PROPYLAMINE; UNCLASSIFIED DRUG;

ALLYLATION; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; CYTOMEGALOVIRUS; CYTOTOXICITY; DECARBOXYLATION; DERIVATIZATION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN TISSUE; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; VACCINIA VIRUS; VARICELLA ZOSTER VIRUS; VESICULAR STOMATITIS VIRUS;

ALNUS;

EID: 78651353029     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.097     Document Type: Article

References (27)

1. L. Agrofoglo, E. Suhas, A. Farese, R. Condom, S.R. Challand, R.A. Earl, and R. Guedj Tetrahedron 50 1994 10611
2. M.T. Crimmins Tetrahedron 54 1998 9229
3. R. Vince, and M. Hua J. Med. Chem. 33 1990 17
4. D.C. Orr, H.T. Figueiredo, C.-L. Mo, C.R. Penn, and J.M. Cameron J. Biol. Chem. 267 1992 4177
5. S.M. Daluge, S.S. Good, M.B. Faletto, W.H. Miller, S. Clair, M.H., L.R. Boone, M. Tisdale, N.R. Parry, J.E. Reardon, R.E. Dornsife, D.R. Averett, and T.A. Krenitsky Antimicrob. Agents Chemother. 41 1997 1082
6. E.N. Fung, Z. Cai, T.C. Burnette, and A.K. Sinhababu J. Chromatogr., B 754 2001 285
7. R.H. Foster, and D. Failds Drugs 55 1998 729
8. J. Melroy, and V. Nair Curr. Pharm. Des. 11 2005 3847
9. G.J. Yuen, S. Weller, and G.E. Pakes Clin. Pharm. 47 2008 351
10. M. Yang, and S.W. Schneller Bioorg. Med. Chem. Lett. 15 2005 149
11. S.M. Roberts, and M.F. Jones J. Chem. Soc., Perkin Trans. 1 1988 2927
12. H.E. Olivo, and J. Yu Tetrahedron: Asymmetry 8 1997 3785
13. H. Rhee, D. Yoon, and M.E. Jung Nucleosides, Nucleotides Nucleic Acids 19 2000 619
14. A.B. Akella, and R. Vince Tetrahedron 52 1996 2789
15. MX.-W. Jiang, B. Jin, J.L. Gage, A. Priour, G. Savela, and M.J. Miller J. Org. Chem. 71 2006 4164
16. F. Li, J.B. Brogan, J.L. Gage, D. Zhang, and M.J. Miller J. Org. Chem. 69 2004 4538
17. C. Cesario, and M.J. Miller J. Org. Chem. 74 2009 5730
18. C. Cesario, L. Tardibono, and M.J. Miller Tetrahedron Lett. 51 2010 3053
19. M.J. Mulvihill, J.L. Gage, and M.J. Miller J. Org. Chem. 63 1998 3357
20. For N-O bond reductions of cycloadducts, see: C. Cesario, L. Tardibono, and M.J. Miller J. Org. Chem. 74 2009 448
21. L. Tardibono, J. Patzner, C. Cesario, and M. Miller J. Org. Lett. 11 2009 4076
22. For examples of guanine base formation, see:
23. C. Balo, J.M. Blanco, F. Fernandez, E. Lens, and C. Lopez Tetrahedron 54 1998 2833
24. 2-((1R,4R)-4-((2,5-Diamino-6-ethoxypyrimidin-4-yl)amino) cyclopent-2-en-1-yl)ethanol was identified (by LC-MS) as a byproduct when the reaction was conducted in EtOH.
25. 2-((1R,4R)-4-(2-Amino-6-ethoxy-9H-purin-9-yl)cyclopent-2-en-1-yl)ethanol was identified (by LC-MS) as a byproduct when prolonged reaction times were allowed.
26. A. Grumann, H. Marley, and R.J.K. Taylor Tetrahedron Lett. 36 1995 7767
27. Detailed antiviral assay data for (-)-3a, (-)-3b, (+)-4a, (+)-4b, and related intermediates can be found in the Supplementary data.