Addition of an apiosyl radical to activated olefins - Synthesis of C-apiosyl compounds

Article abstract of DOI:10.1055/s-1996-4407

3'-O-Benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanosyl bromide (8), prepared in two steps from 2,3-O-isopropylidene-D-apio-β-D-furanose (6), was reacted with tris(trimethylsilyl)silane/AIBN in the presence of an excess of a variety of activated olefins such as dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, crotonaldehyde, cyclopent-2-enone, and cyclohex-2-enone to afford the corresponding C-apiosides 10 having β-configuration.