Catalytic ferrier rearrangement of unsaturated nucleosides

Article abstract of DOI:10.1016/S0040-4039(98)02264-3

The attempted intermolecular addition of malonyl radicals to 1',2'- unsaturated nucleosides has led to the unexpected formation of furanones. Thus, only catalytic amounts of ceric(IV) ammonium nitrate (CAN), induce a Ferrier rearrangement. The unsaturated lactone was isolated in good yield and can serve as a precursor for the synthesis of optically active products.