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 Introduction

2 ortho-Functionalization of Phenols and Aniline Derivatives Mediated by Iodanes (III) and Synthesis of Panacene

2.1 Cross-Coupling with Aniline Derivatives

2.2 Dearomative Cycloaddition of Arenes and Heteroarenes

2.3 Total Synthesis of Panacene

3 meta-Functionalization of Aniline Derivatives and Synthesis of Erysotramidine

3.1 meta-Functionalization of Aniline Derivatives

3.2 Total Synthesis of Erysotramidine

4 para-Functionalization of Phenols and Applications in Total Synthesis

4.1 Bimolecular Approach Mediated by Protecting Groups

4.2 ipso-Rearrangement

4.3 Oxidative Alkyl Shift

4.4 Oxidative Prins-Pinacol Rearrangement

4.5 Oxidative Prins-Type Reaction

4.6 Total Synthesis of (–)-Fortucine

4.7 Total Synthesis of Isostrychnine

4.8 Total Synthesis of (–)-Strychnopivotine

5 Development of a Functional Protecting Group

Key words

phenols - anilines - hypervalent iodines - aromatic umpolung - total synthesis

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