A new reaction manifold for the Barton radical intermediates: Synthesis of N-heterocyclic furanosides and pyranosides via the formation of the C1-C2 bond

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1492-1493

  Rhee, Jong Uk ^a   Bliss, Brian I ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CARBOHYDRATE; CYCLOHEXANE; FURAN DERIVATIVE; FURANOSIDE DERIVATIVE; IMIDAZOLE DERIVATIVE; PYRANOSIDE; RADICAL; THIOURETHANE DERIVATIVE; UNCLASSIFIED DRUG; URETHAN DERIVATIVE; XANTHIC ACID DERIVATIVE;

ARTICLE; BARTON MCCOMBIE REACTION; CHEMICAL BOND; CHEMICAL REACTION; CONFORMATION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0037433267     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028617z     Document Type: Article

References (36)

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19. For reviews of N-heterocyclic glycosides, see: (a) Garner, P. Synthetic Approaches to Complex Nucleoside Antibiotics. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988: Vol. 1, Part A, pp 397-434. (b) Knapp, S. Chem. Rev. 1995, 95, 1859. (c) Vorbrüggen, H. Handbook of Nucleoside Synthesis; Wiley: New York, 2001.
20. For reviews of N-heterocyclic glycosides, see: (a) Garner, P. Synthetic Approaches to Complex Nucleoside Antibiotics. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988: Vol. 1, Part A, pp 397-434. (b) Knapp, S. Chem. Rev. 1995, 95, 1859. (c) Vorbrüggen, H. Handbook of Nucleoside Synthesis; Wiley: New York, 2001.
21. 2-branched sugars see: (a) Linker, T.; Sommermann, T.; Kahlenberg, F. J. Am. Chem. Soc. 1997, 120, 9377. (b) Beyer, J.; Madsen, R. J. Am. Chem. Soc. 1998, 120, 12137.
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23. Radical 1 has previously been identified by EPR methods. For a discussion of the mechanism of Barton deoxygenation see: (a) Barton, D. H. R.; Crich, D.; Löbberding, A.; Zard, S. Z. Tetrahedron 1986, 42, 2329. (b) Forrest, D.; Ingold, K. U.; Barton, D. H. R. J. Phys. Chem. 1977, 81, 915. (c) Barker, P. J.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1984, 683.
24. Radical 1 has previously been identified by EPR methods. For a discussion of the mechanism of Barton deoxygenation see: (a) Barton, D. H. R.; Crich, D.; Löbberding, A.; Zard, S. Z. Tetrahedron 1986, 42, 2329. (b) Forrest, D.; Ingold, K. U.; Barton, D. H. R. J. Phys. Chem. 1977, 81, 915. (c) Barker, P. J.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1984, 683.
25. Radical 1 has previously been identified by EPR methods. For a discussion of the mechanism of Barton deoxygenation see: (a) Barton, D. H. R.; Crich, D.; Löbberding, A.; Zard, S. Z. Tetrahedron 1986, 42, 2329. (b) Forrest, D.; Ingold, K. U.; Barton, D. H. R. J. Phys. Chem. 1977, 81, 915. (c) Barker, P. J.; Beckwith, A. L. J. J. Chem. Soc., Chem. Commun. 1984, 683.
26. 12 (Huang, G.; Hollingsworth, R. I. Tetrahedron 1998, 54, 1355).
27. See Supporting Information for details.
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36. For another example of such difference between the geometrical isomers of the acceptor see: Enholm, E. J.; Trivellas A. J. Am. Chem. Soc. 1989, 111, 6463.