Methyl esters from vernonia oil containing cis-12,13-epoxy-cis-9-octadeeenoate were reacted with acetone in the presence of a boron trifluoride catalyst to yield trans-12,13-O-isopropylidene-9ene derivative I. Epoxidation of the unsaturation followed by reaction with acetone gave the isomeric trans,trans-di-O-isopropylidene derivatives III of 9,10:12,13-tetrahydroxystearates. The carboxylie acids of III were converted to vinyl esters and subsequent hydrolysis of the isopropylidene groups with boric acid produced vinyl threo-9,10-threo-12,13-tetrahydroxystearates. By the same sequence of reactions monoepoxidized methyl linoleate yielded an optically inactive derivative which had identical refractive index, Ig spectrum, and GLC data to III from vernonia methyl esters.
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