THE FIRST SYNTHESIS OF ALL POSSIBLE STEREOISOMERS OF THE (E)-4,5-DIHYDROXYDEC-2-ENAL, IN HOMOCHIRAL FORM

The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.