A Stereoselective Synthesis of (3<i>E</i>,5<i>Z</i>)-3,5-Tetradecadienoic Acid (Megatomoic Acid), the Sex Attractant of the Black Carpet Beetle

Abstract

Abstract The total synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) is accomplished with 74% stereoselectivity through the use of stereoselective rearrangement of ethyl 3,4-tridecadienoate to ethyl (2E,4Z)-2,4-tridecadienoate with alumina and the extension of the carbon chain with methyl methylthiomethyl sulfone.