Spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives

Abstract

The attachment of a dimethylallyl moiety to C4 of 1,3-dihydroxynaphthalene led to spontaneous oxidative cyclisations, resulting in the formation of two tetrahydrobenzofuran and one bicyclo[3.3.1]nonane derivatives. Incubation under an ¹⁸O-rich atmosphere proved that both the incorporated oxygen atoms originated from O₂. A radical-involved mechanism is proposed for these cyclisations.