Rapid Formation of Advanced Scaffolds from Phenols and Anilines

Abstract

This article is an account of our efforts over the last decade to functionalize phenols and anilines at any position and to use these compounds to generate substituted aromatic systems and advanced unsaturated cyclohexanone moieties, enabling the rapid formation of complex structures. Total syntheses of numerous natural products involving such intermediates were achieved.1 Introduction2 ortho-Functionalization of Phenols and Aniline Derivatives Mediated by Iodanes (III) and Synthesis of Panacene2.1 Cross-Coupling with Aniline Derivatives2.2 Dearomative Cycloaddition of Arenes and Heteroarenes2.3 Total Synthesis of Panacene3 meta-Functionalization of Aniline Derivatives and Synthesis of Erysotramidine3.1 meta-Functionalization of Aniline Derivatives3.2 Total Synthesis of Erysotramidine4 para-Functionalization of Phenols and Applications in Total Synthesis4.1 Bimolecular Approach Mediated by Protecting Groups4.2 ipso-Rearrangement4.3 Oxidative Alkyl Shift4.4 Oxidative Prins-Pinacol Rearrangement4.5 Oxidative Prins-Type Reaction4.6 Total Synthesis of (–)-Fortucine4.7 Total Synthesis of Isostrychnine4.8 Total Synthesis of (–)-Strychnopivotine5 Development of a Functional Protecting Group