Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir

Organic and Biomolecular Chemistry

Volumn 10, Issue 9, 2012, Pages 1870-1876

  Boyle, Grant A ^a   Edlin, Christopher D ^a   Li, Yongfeng ^b   Liotta, Dennis C ^b   Morgans, Garreth L ^a   Musonda, Chitalu C ^a  

^a iThemba Pharmaceuticals (Pty) Ltd   (South Africa)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABACAVIR; CARBOCYCLIC NUCLEOSIDES; ELECTRON WITHDRAWING GROUP; ENANTIOPURE; ENANTIOSELECTIVE SYNTHESIS; MEDIATED REACTIONS; TETRABUTYLAMMONIUM SALTS; TOTAL SYNTHESIS;

POSITIVE IONS;

CHEMISTRY;

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ABACAVIR; CHOLINESTERASE; TRIACYLGLYCEROL LIPASE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; ENZYMOLOGY; METABOLISM; PSEUDOMONAS FLUORESCENS; STEREOISOMERISM; SWINE; SYNTHESIS;

ANIMALS; CHOLINESTERASES; DIDEOXYNUCLEOSIDES; LIPASE; MOLECULAR STRUCTURE; PSEUDOMONAS FLUORESCENS; STEREOISOMERISM; SWINE;

EID: 84863161794     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob06775g     Document Type: Article

References (36)

1. E. De Clercq "The design of drugs for HIV and HCV" Nat. Rev. Drug Discovery 2007 6 1001
2. D. M. Huryn M. Okabe Chem. Rev. 1992 92 1745
3. C. Simons, Nucleoside Mimetics: Their Chemistry and Biological Properties, Gordon and Breach Science Publishers, Amsterdam, 2001
4. G. N. Jenkins N. J. Turner Chem. Soc. Rev. 1995 24 169
5. M. Asami J. Takahashi S. Inoue Tetrahedron: Asymmetry 1994 5 1649
6. B. M. Trost G.-H. Kuo T. Benneche J. Am. Chem. Soc. 1988 110 621
7. B. M. Trost L. Li S. D. Guile J. Am. Chem. Soc. 1992 114 8754
8. B. M. Trost R. Madsen S. D. Guile A. E. H. Elia Angew. Chem., Int. Ed. Engl. 1996 35 1569
9. B. M. Trost R. Madsen S. D. Guile B. Brown J. Am. Chem. Soc. 2000 122 5947
10. B. M. Trost M. Osipov P. S. J. Kaib M. T. Sorum Org. Lett. 2011 13 3222
11. J. R Huff Bioorg. Med. Chem. 1999 7 2667
12. M. Tanaka Y. Norimine T. Fujita H. Suemune K. Sukai J. Org. Chem. 1996 61 6952
13. M. Tanaka M. Yoshioka K. Sakai Tetrahedron: Asymmetry 1993 4 981
14. M. E. Jung H. Rhee J. Org. Chem. 1994 59 4719
15. M. T. Crimmins Tetrahedron 1998 54 9229
16. C. A. M. Afonso V. B. Kurteva Chem. Rev. 2000 109 6809
17. R. Vince M. Hua J. Brownell S. M. Daluge F. C. Lee W. M. Shannon G. C. Lavelle J. Quails O. S Weislow R. Kiser P. G. Canonico R. H. Schultz V. L. Narayanan J. G. Mayo R. H. Shoemaker M. R. Boyd Biochem. Biophys. Res. Commun. 1988 156 1046
18. S. J. C. Taylor R. McCague R. Wisdom C. Lee K. Dickson G. Ruecroft F. O'Brien J. Littlechild J. Bevan S. M Roberts C. T. Evans Tetrahedron: Asymmetry 1993 4 1117
19. M. J. Mulvihill J. A. Gage M. J. Miller J. Org. Chem. 1998 63 3357
20. C. Kaneko A. Sugimoto S. Tanaka Synthesis 1974 876
21. D. R. Deardorff C. Q. Windham C. L. Craney1 Org. Synth. 1996 73 25
22. K. Laumen M. P. Schneider J. Chem. Soc., Chem. Commun. 1986 1298
23. E. Forró F. Fülöp Tetrahedron: Asymmetry 2004 15 573
24. N. Katagiri M. Takebayashi H. Kokufuda C. Kaneko K. Kanehira M. Torihara J. Org. Chem. 1997 62 1580
25. A. Vazquez-Romero J. Rodriguez A. Lledo X. Verdaguer A. Riera Org. Lett. 2008 10 4509
26. A. Kim J. H. Hong Bull. Korean Chem. Soc. 2007 28 1545
27. M. Freiria A. J. Whitehead W. B. Motherwell Synthesis 2005 18 3079
28. G.-I. An H. Rhee Nucleosides, Nucleotides Nucleic Acids 2002 21 65
29. M. T. Crimmins B. W King W. J. Zuercher A. L. Choy J. Org. Chem. 2000 65 8499
30. S. M. Daluge M. T. Martin B. R. Sickles D. A. Livingston Nucleosides, Nucleotides Nucleic Acids 2000 19 297
31. M. T. Crimmins W. J. Zuercher Org. Lett. 2000 2 1065
32. H. F. Olivo J. Yu J. Chem. Soc. Perkin Trans. 1 1998 3 391
33. S. M. Daluge S. S. Good M. B. Faletto W. H. Miller M. H St. Clair L. R. Boone M. Tisdale N. R. Parry J. E. Reardon R. E. Dornsife D. R. Averett T. A Krenitsky Antimicrob. Agents and Chem. 1997 41 1082
34. M. T. Crimmins B. W. King J. Org. Chem. 1996 61 4192
35. L. Kiss E. Forró R. Sillanpaa F. Fülöp J. Org. Chem. 2007 72 8786
36. T. Durst M. J. O'sullivan J. Org. Chem. 1970 56 2043