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-vinyl-pyridine 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 tocopherylquinones, thus suggesting, for the first time, a drawback effect of the oxidative metabolism on the antiviral activity of these compounds. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.