Synthesis 2005(20): 3549-3554  
DOI: 10.1055/s-2005-918420
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Franco Fernándeza, Xerardo García-Mera*a, Carmen Lópeza, Melvin Moralesa, José Enrique Rodríguez-Borgesb
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
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Publikationsverlauf

Received 3 June 2005
Publikationsdatum:
06. Oktober 2005 (online)

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.