Research for new organic compounds which may show potential antitumor and antiviral activity leads to the discovery of effective medications. Modified nucleosides are significant class of compounds showing therapeutic activity. Recently a number of studies describing modified heterocyclic nucleosides with isoxazolidinyl ring instead of sugar moiety has appeared [1]. The most convenient method of synthesis modified isoxazolidinyl nucleosides are reactions of N-vinyl derivatives of nucleic acid bases with corresponding nitrone. However there are only few studies reporting synthesis of isoxazolidinyl and izoxazolyl C-C nucleosides.

We would like to present results of  studies on synthesis of modified C-C nucleosides in which sugar moiety has been replaced with fluorinated isoxazolidinyl ring. Fluorinated analogues with potential biological activity attract more attention due to their unique properties, which are so important in biochemistry and medical chemistry.

Synthesis of fluorinated 5-vinylpyrimidine as diporalophile in 1,3-dipolar cycloaddition with selected nitrones will be described in some details [2]. 

References:

[1]  A. Leggio, A. Liguori, L. Maiuolo, A. Napoli, A. Procopio, C. Siciliano, G. Sindona, J. Chem. Soc., Perkin Trans. 1 (1997) 3097-3099.

[2]   U. Chiacchio, A. Padwa, G. Romeo, Curr. Org. Chem. 13 (2009) 422-447.

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1. Fluorinated carbanucleosides and acyclic nucleosides