4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5- analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis

Article abstract of DOI:10.1016/S0040-4020(01)81757-9

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 α-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.