A Short and Convenient Synthesis of New 1,2-Disubstituted Carbocyclic Nucleoside Analogues of Pyrimidine Based on a Cyclopentene Ring

M. J. González-Moa; P. Besada; M. Teijeira; C. Terán; E. Uriarte

doi:10.1055/s-2004-815975

PAPER

A Short and Convenient Synthesis of New 1,2-Disubstituted Carbocyclic Nucleoside Analogues of Pyrimidine Based on a Cyclopentene Ring

M. J. González-Moa^a, P. Besada^a, M. Teijeira^a, C. Terán*^a, E. Uriarte^b
^a Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Vigo, 36200 Vigo, Spain
Fax: +34(986)812262; e-Mail: mcteran@uvigo.es;
^b Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain

Abstract

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Abstract

The synthesis of a new series of 1,2-disubstituted carbonucleoside analogues, pyrimidines of general structure I, is reported. These compounds were prepared in good yield from (±)-6-azabicyclo[3.2.0]hept-3-en-7-one (1) via two synthetic routes that involve NaBH₄-mediated C-N bond cleavage as the key step. The uracil derivative Ia was halogenated with Cl, Br, and I at position 5 by treatment with the corresponding N-halosuccinimide.

Key words

nucleosides - reductions - amino alcohols - carbocycles - heterocycles

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References

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