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-0 bond, a β-keto ester is formed that can be reacted with a bis-nucleophile to yield a new C-nucleoside analogue.
ASJC Scopus subject areas
- Organic Chemistry