A novel and efficient synthesis of tocopheryl quinones by homogeneous and heterogeneous methyltrioxorhenium/hydrogen peroxide catalytic systems

A convenient and efficient application of heterogeneous poly(4-vinylpyridine), poly(4-vinylpyridine N-oxide), and polystyrene/methylrhenium trioxide systems for the selective oxidation of tocopherols and tocopherol derivatives to the corresponding ortho- and para-tocopherylquinones is described. Environment friendly, easily available, and low-cost hydrogen peroxide (H2O2) was used as the oxygen atom donor. The antiviral activity of the newly synthesized tocopherylquinones and their parent tocopherols against influenza A virus is also reported. On the basis of the biological assay, the activity of tocopherols against influenza virus is higher than that showed by the corresponding tocopheryl-quinones, thus suggesting, for the first time, a drawback effect of the oxidative metabolism on the antiviral activity of these compounds.