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

Article abstract of DOI:10.1246/bcsj.56.3521

The total synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) is accomplished with 74percent 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.