Synthesis of fused 1,2-naphthoquinones with cytotoxic activity using a one-pot three-step reaction

A method for the synthesis of fused 1,2-naphthoquinones, as analogues of biologically active natural terpene quinones, is described. The intermediate polycyclic naphthalenes were prepared by a one-pot palladium-catalysed process from simple alkynes, one of which was made from an optically pure biomass-derived levoglucosenone. The prepared methoxy-substituted naphthalenes were subsequently transformed in one step to 1,2-naphthoquinones by a trivalent-iodine-mediated oxidation. The naphthoquinone products were found to have cytotoxic properties. Biologically active 1,2-naphthoquinones, structurally related to natural products, were synthesised using a palladium-catalysed tandem reaction to form naphthalenes, followed by oxidation with trivalent iodine reagents.