The Nitrile Oxide Cycloaddition (NOC) Route to a Multipurpose C-Nucleoside Intermediate: A New Class of C-Nucleosides

Article abstract of DOI:10.1021/jo00155a054

A new route to the important class of antibiotic and antiviral agents, the C-nucleosides, has been developed.The nitrile oxide generated from a protected derivative of β-D-ribofuranosylnitromethane has been shown to react with ethoxyacetylene to deliver an isoxazole C-nucleoside.On hydrogenolytic cleavage of the N-O bond, a β-keto ester is formed that can be reacted with a bisnucleophile to yield a new C-nucleoside analogue.