SYNTHESIS OF 9-OXONONANOYL CHOLESTEROL BY OZONIZATION

A new route for the preparation of 9-oxononanoyl cholesterol (5) and i ts stable dimethylacetal (4) is described. The core aldehyde 5 is one of the major products formed during lipid peroxidation, The synthesis starts with the ozonization of oleic acid in methanol and further redu ction with dimethyl sulfide to yield 9,9-dimethoxy nonanoic acid (2a). The condensation of 2a with cholesterol is achieved with N,N'-dicyclo hexylcarbodiimide in dichloromethane to give 4. Further hydrolysis of 4 with the help of an acidic ion exchange resin yields 9-oxononanoyl c holesterol.