Biomimetic synthesis of the dinaphthofuranquinone violet-quinone, utilizing oxidative dimerization with the ZrO2/O2 system

The first total and biomimetic synthesis of violet-quinone (), which has a dinaphthofuranquinone (DNFQ) framework, is described. This synthesis features the oxidative dimerization of 1-naphthol and the construction of the DNFQ framework by photochemical ring closure of 2,2′-binaphthoquinone as a key intermediate. Compound was prepared by the novel oxidative dimerization of with a semiconductor (such as ZrO2) in the presence of dioxygen, followed by oxidation of the resulting 2,2′-binaphthyl-1,1′-quinone with HNO3.