P. Allevi et al., A PRACTICAL SYNTHESIS OF (R)-(E)-4-HYDROXYALK-2-ENAL AND (S)-(E)-4-HYDROXYALK-2-ENAL, CYTOTOXIC PRODUCTS OF THE MICROSOMAL LIPID-PEROXIDATION, Tetrahedron : asymmetry, 5(5), 1994, pp. 927-934
The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals,
important products of lipid peroxidation (LPO), has been carried out v
ia enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediat
es obtained from two diastereomeric diepoxides deriving from D-mannito
l. These aldehydes were transformed into the final compounds by Wittig
condensation with (formylmethylene)triphenylphosphorane and regenerat
ion of the hydroxy group.