Synthesis and determination of cis or trans isoprostane precursors by a 1H NMR NOE study

Abstract

Different isoprostane precursors have been synthesized from a 5-iodo-sugar via a radical cyclization initiated by azoisobutyronitrile (AIBN)–Et₃B. The NOE ¹H NMR experiment is a simple and efficient method for the determination of the relative functional configuration of tetrasubstituted cyclopentane derivatives. Applied to chiral lactone structures or hydroxy esters, this method allows the determination a priori of their relative configuration.