Dihydronaphthofurans: synthetic strategies and applications

Abstract

Dihydronaphthofurans (DHNs) are an important class of arene ring-fused furans which are widely found in many natural and non-natural products and drug candidates with relevant biological and pharmacological activities. Furthermore, vinylidene-naphthofurans exhibit photochromic properties when exposed to UV or sun light at room temperature. For these reasons, a vast array of synthetic procedures for the preparation of dihydronaphthofurans including annulation of naphthols with various reagents, cycloaddition reactions ([3 + 2], [4 + 1] and Diels–Alder), intramolecular transannulation, Friedel–Crafts, Wittig, Claisen rearrangement, neophyl rearrangement and other reactions under various conditions have been developed over the past decades. This review aims to describe the different strategies developed so far for the synthesis of dihydronaphthofurans and their applications. After a brief introduction to the types of dihydronaphthofurans and their biological activities, the different synthetic approaches such as chemical, photochemical, and electrochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. The subsequent section focuses on biological and pharmacological applications and photochromic properties of the target compounds.