On the way towards a new total synthesis of (S)-arogenate, a novel aryl-λ³-iodane-mediated oxidative spirocyclization of para-substituted phenol derivatives has been discovered. Starting from easy accessible 2-(4-hydroxybenzamido)acrylates we could construct spirocyclic lactams in up to 52% yield. Under alternative reaction conditions the same precursors underwent an unexpected oxidative spirocyclization yielding a novel δ-spirolactone in up to 70% yield.