A deconstruction-reconstruction strategy to access 1-naphthol derivatives: application to the synthesis of aristolactam scaffolds

A deconstruction-reconstruction strategy for the synthesis of multisubstituted polycyclic aromatic hydrocarbons (PAHs) is delineated herein. The deconstruction step enables the synthesis of o -cyanomethylaroyl fluorides that are bifunctional substrates holding both a pro-nucleophile and an electrophile. The construction step involves a formal [4 + 2] benzannulation using o -cyanomethylaroyl fluorides and active methylenes. The utility of this synthetic method is also demonstrated by the synthesis of a tetracyclic aristolactam derivative. A fragmentation-annulation reaction of α-oximinoindanones for the synthesis of 1-naphthol derivatives has been delineated in a highly practical manner. The utility was further demonstrated in the multi-step synthesis of a tetracyclic aristolactam analogue.