THE FIRST SYNTHESIS OF THREO-(E)-4,5-DIHYDROXYDEC-2-ENAL AND ERYTHRO-(E)-4,5-DIHYDROXYDEC-2-ENAL CARBONYLS RELATED TO THE PEROXIDATION OF LIVER MICROSOMAL LIPIDS

The first synthesis of three and erythro (E)-4,5-dihydroxydec-2-enals, aldehydes related to the lipid peroxidation is accomplished by reaction of alpha-benzoyloxheptanal with the Grignard reagent of 3,3-diethoxy-1-propyne and lithium aluminum hydride reduction. Acetonization of the diol system allows a simple chromatographic separation of the diastereoisomers, the geometry of which was established by H-1 and C-13 NMR experiments and was confirmed by an independent synthesis of (E,4R,5R)-4,5-O-isopropylidene-4,5-dihydroxydec-2-enal from D-mannitol