Oxidative Prins-Pinacol Tandem Process Mediated by a Hypervalent Iodine Reagent: Scope, Limitations, and Applications

An oxidative Prins-pinacol tandem process mediated by a hypervalent iodine reagent has been developed. This oxidative version of the famous tandem process fits within the concept of "aromatic ring umpolung" and allows the stereoselective transformation of simple phenols into highly elaborated spirocyclic dienone cores containing several quaternary carbon centers. The scope and the limitations of this process, including the study of its stereoselectivity, are described in this article. As a direct application of this stereoselective process, we describe the formal synthesis of (-)-platensimycin, an important antibiotic agent.