Electrooxidative Dearomatization to Spiroisoxazolines: Application to Total Synthesis of Xanthoisoxazoline B
Dengfeng Chen, Tianyu He, Yongcan Jin, Shenlin Huang
Abstract
Abstract The synthesis of spiroisoxazoline molecules has been developed via anodic oxidative dearomatization of 4‐methoxybenzyl oximes. The reaction is thought to proceed through 5‐ exo C−O bond‐forming cyclization of oxime radicals with arenes on the basis of cyclic voltammetry studies. Moreover, spiroisoxazolines can be built directly from readily available carbonyl tethered phenolics via an oximation/dearomatization cascade. Using this spiroisoxazolization as the key step, the first total synthesis of xanthoisoxazoline B has been achieved in three steps. magnified image
Topics & Concepts
ChemistryTotal synthesisOximeRadicalCyclic voltammetryCombinatorial chemistryMoleculeStereochemistryOrganic chemistryElectrochemistryElectrodePhysical chemistryRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods