Syntheses and reactions of methyl (Z)-9, 10-epoxy-13-oxo-(E)-11-octadecenoate and methyl (E)-9, 10-epoxy-13-oxo-(E)-11-octadecenoate

FJ Hidalgo, R Zamora, E Vioque - Chemistry and physics of lipids, 1992 - Elsevier
The syntheses and reactions of two epoxyketoacids (methyl (Z)-9, 10-epoxy-13-oxo-(E)-11-
octadecenoate (IV) and methyl (E)-9, 10-epoxy-13-oxo-(E)-11-octadecenoate (V)) are
described. The synthetic method is based on the stereoselective oxidation of linoleic acid by
soybean lipoxygenase to produce the corresponding 13-hydroperoxide. Reduction of the
hydroperoxide with sodium borohydride followed by oxidation, esterification and epoxidation
yielded the compounds IV and V with a global yield of 14% and 3%, respectively, referred to …