A new, mild, radical route for the synthesis of 3-substituted maleimides has been developed. This new method incorporates alkene hydroboration, conjugate addition-aminoxylation and TEMPO-H elimination in a one-pot procedure, using cheap, readily available starting materials. A variety of 3-substituted maleimides have been prepared in good to excellent yield.

Both (±)-protoemetinol, its 3-epi-isomer and (±)-3-desmethyl protoemetinol have been prepared in five linear steps from a dihydroisoquinoline using a 6-exo-trig cyclisation of a vinyl radical in the key step. This novel and particularly short route has potential application in the synthesis of Alangium and Mitragyna alkaloids.