Molecular Complexity from Aromatics: Recent Advances in the Chemistry of paraQuinol and Masked para-Quinone Monoketal

Synthesis of complex organic molecules from simple, cheap, and readily available starting materials is one of the most challenging and desirable factors in organic synthesis. In the last two decades, various methods have been developed for the de-aromatization reaction of planar aromatics compounds which lead to reactive intermediates like 2,5-cyclohexadienone ketal and para-quinol having a non-planar framework. Recently, there is an upsurge of interest in the development of the chemistry of these intermediates due to their inherent dual electrophilic and nucleophilic character. The presence of diverse functionality makes them important scaffolds and thus these are intensively utilized for the development of methodologies towards the synthesis of the highly functionalized and diverse chemical framework. These synthons have also been used in the total synthesis of many natural products. Interestingly, these are also adaptable for asymmetric synthesis. This review is a summary of the recent development of methods for 2,5-cyclohexadienone ketal and para-quinol synthesis and their application in natural product synthesis.