Abstract
AbstractThe reaction of methyl octadec‐trans‐11‐en‐9‐ynoate (1) with mercuric sulfate in the presence or absence of sulfuric acid is described. Treatment of 1 with mercuric sulfate in absolute methanol yielded methyl 9(10)‐oxoocta‐dec‐trans‐11‐enoates (Product A). This product, upon treatment withm‐chloroperbenzoic acid, afforded methyltrans‐11,12‐epoxy‐9‐oxooctadecanoate (4) and methyl 10‐oxooctadec‐trans‐11‐enoate (2). Sodium borohydride reduction of A furnished the corresponding hydroxy esters. The treatment of 1 with mercuric sulfate in the presence of sulfuric acid gave as major product methyl 9(10)‐oxo‐11(12)‐methoxyoctadecanoates and methyl 9(10)‐oxoocta‐dec‐trans‐11‐enoates as a minor product. When methyl 11,12‐epoxyoctadec‐9‐ynoate was reacted with acid in methanol, methyl 12‐hydroxy‐11‐methoxyoctadec‐9‐ynoate was formed, which on treatment with zinc chloride in CCl4 yielded methyl 9,12‐epoxyoctadec‐9,11‐dienoate exclusively. The preparation of oxo fatty esters from the total methyl esters ofSantalum album was also demonstrated. The structures of the products were established by chemical derivatization and spectral characterization.
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