{Catalytic Ferrier rearrangement of unsaturated nucleosides}


Linker T, Sommermann T, Gimisis T, Chatgilialoglu C. {Catalytic Ferrier rearrangement of unsaturated nucleosides}. Tetrahedron Lett. [Internet]. 1998;39:9637–9638.


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.