Fluorinated analogs of nucleosides find use as antiviral and anticancer agents. This is possible due to their ability to act as inhibitors of nucleotide metabolism- they are indistinguishable by active site of enzymes. Properties of fluorine atom are very important here (similar size to the hydrogen atom, large electronegativity, the possibility of replacing a hydroxyl group).
Interesting examples of nucleoside derivatives with bioactive properties are acyclic nucleosides and carbanucleosides, reffered to in our work.
In recent years, a number of studies describing isoxazolidinyl analogs of nucleosides with isoxazolidinyl ring instead of sugar moiety has appeared. These compounds, which have N-O bond in the five-membered ring, are prone to breaking in appropriate conditions [1].
Products of opening isoxazolidinyl ring can be classified both as a 1,3-aminoalcohols as well as acyclic nucleosides.

Our synthetic task was to obtain presented above nitrone (1) from the respective purine bases. These compounds would be subjected to the 1,3-dipolar cycloaddition with fluorinated olefins. Next step would be reaction of opening isoxazolidinyl ring.

References:

[1] Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Albert Padwa and William H. Pearson, John Wiley & Sons, 2003

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1. Modified isoxazolidinyl nucleosides