Synthetic Routes to Benzanthracenes via Transient 1-Benzylisobenzofuran Derivatives

Article abstract of DOI:10.1021/jo00336a004

A synthetic route to 7-acetoxybenzanthracenes is described based on the generation of 1-benzylisobenzofurans and their capture with methyl acrylate in a Diels-Alder reaction.The 1,4-epoxy-1,2,3,4-tetrahydronaphthalene derivatives so formed are aromatized to naphthoate esters under acidic conditions and hydrolyzed to the naphthoic acids, and these are cyclized to the 7-acetoxybenzanthracenes with zinc chloride in acetic anhydride.