Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation

The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups