Site‐selective Oxidative Dearomatization of Phenols and Naphthols into ortho‐Quinols or Epoxy ortho‐Quinols using Oxone as the Source of Dimethyldioxirane

Abstract

AbstractA novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho‐quinols or epoxy ortho‐quinols from a site‐selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step.magnified image