Novel 1,2-Disubstituted Carbocyclic Nucleoside Analogues of Purine with a Cyclopentene Ring

Abstract

A total and versatile synthesis of a new series of carbocyclic nucleoside analogues which are derivatives of purine with a 1,2-disubstituted cyclopentene ring (I) is described. The 6-chloropurine derivatives 3 and 9 were prepared by construction of the heterocyclic base about the primary amino group of the (±)-cis-2-amino-3-cyclopentenylmethanol (1), which was synthesized in good yield from cyclopentadiene in four steps. The substitution of a chlorine atom in the compounds 3 and 9 by an amino group (compounds 4 and 10) and by a hydroxyl group (compounds 5 and 11) was carried out with NH₄OH or with NaOH, respectively.

Key words

amino alcohol - nucleosides - heterocycles - cyclization - nucleophilic aromatic substitution

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