Oxidative ipso-Rearrangement Performed by a Hypervalent Iodine Reagent and Its Application

An oxidative ipso-rearrangement mediated by a hypervalent iodine reagent that enables rapid generation of a functionalized dienone system containing a quaternary carbon center connected to several sp(2) centers has been developed. The process occurs through transfer of an aryl group from a silyl segment present on the lateral chain. As an illustration of the potential of this transformation, a total synthesis of sceletenone, a small alkaloid, is described.