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Synthesis 2004(12): 1991-1995  
DOI: 10.1055/s-2004-829141
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Biological Evaluation of Carbocyclic Nucleosides with 2′,3′-Dihomo-xylo-carbocyclic or Carbocyclic Fused to a Tetrahydrofuran Ring

María José Figueiraa, Olga Caamañoa, Franco Fernández*a, J. Enrique Rodríguez-Borgesb, Jan Balzarinic, Erik De Clercqc
a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: qofranco@usc.es;
b CIQ/Departamento de Química, Facultade de Ciencias, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal
c Rega Institute for Medical Research, Katholieke Universiteit Leuven, 3000 Leuven, Belgium
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Publication History

Received 21 April 2004
Publication Date:
13 July 2004 (online)

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Abstract

New purinyl 2′,3′-dihomo-xylo-carbocyclic pentafuranosides and carbocyclic nucleosides fused with tetrahydrofuran ring were synthesized from (±)-c-4-amino-r-1,c-2,t-3-cyclopentanetrimethanol (8). The strongly acid medium in which the purine system was completed on pyrimidine derivative 9 caused condensation of the cis-hydroxymethyl groups, giving rise to a 3-oxabicyclo[3.3.0]octane structure. None of the new compounds exhibited more than very modest antiviral or antitumor activity.

Key words

xylo-carbocyclic nucleosides - tetrahydrofuran derivatives - synthesis - antiviral - antitumoral activity

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The crystallographic data of 13 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication No. CCDC 212937. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.