A PRACTICAL SYNTHESIS OF (R)-(E)-4-HYDROXYALK-2-ENAL AND (S)-(E)-4-HYDROXYALK-2-ENAL, CYTOTOXIC PRODUCTS OF THE MICROSOMAL LIPID-PEROXIDATION

The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out via enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediates obtained from two diastereomeric diepoxides deriving from D-mannitol. These aldehydes were transformed into the final compounds by Wittig condensation with (formylmethylene)triphenylphosphorane and regeneration of the hydroxy group.