A Convenient Synthesis of Novel Pyrimidinyl-5′-nor-1′-homocarbanucleosides Based on Indanol

Franco Fernández; Xerardo García-Mera; Carmen López; Melvin Morales; José Enrique Rodríguez-Borges

doi:10.1055/s-2005-918420

PAPER

A Convenient Synthesis of Novel Pyrimidinyl-5′-nor-1′-homocarbanucleosides Based on Indanol

Franco Fernández^a, Xerardo García-Mera*^a, Carmen López^a, Melvin Morales^a, José Enrique Rodríguez-Borges^b
^a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: + 34(981)594912; e-Mail: qoxgmera@usc.es;
^b CIQ, Departamento de Química, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal

Abstract

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Abstract

Starting from (±)-cis-3-hydroxymethyl-1-indanol, novel pyrimidinyl-5′-nor-1′-homocarbanucleosides were synthesized through a key coupling reaction with pyrimidine bases (Mitsunobu reaction for uracil and thymine, and nucleophilic substitution on a mesylate for cytosine). The uracil derivative was 5-halogenated by treatment with N-chloro- or N-bromosuccinimide.

Key words

indan carbanucleosides - Mitsunobu reaction - nucleophilic substitution - antiviral - 5-halopyrimidines

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Referenzen

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