No abstract

The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests.

The N-benzoylamino-2-cyclopenten-1-ol, derived from the nitrosocarbonyl hetero Diels-Alder cycloaddition reaction followed by the mild reductive N-O bond cleavage, allows for the preparation of cyclopentenyl-nucleoside analogues through the palladium(0)-catalyzed addition of both purine and pyrimidine heterobases to the allylic acetate derivative with retention of the starting material stereochemistry. A systematic study is performed on different heterobases to test the general application of the protocol.