4-HYDROXYNON-2-ENAL, A CYTOTOXIC LIPID-PEROXIDATION PRODUCT, AND ITS C-5-ANALOG 4-HYDROXYPENT-2-ENAL - ENANTIOSELECTIVE SYNTHESIS AND STEREOANALYSIS

A stereoselective synthesis of the lipid peroxidation products 4-hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)-catalyzed oxidative degradation and subsequent stereoanalysis of the resulting alpha-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.