HOME / PUBLICATIONS /

{Catalytic Ferrier rearrangement of unsaturated nucleosides}

Citation:

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

Abstract:

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. (C) 1998 Elsevier Science Ltd. All rights reserved.