Identification and Synthesis of a Macrolide as an Anti-aphrodisiac Pheromone from Males of .

Investigation of the contents of the scent glands of the heliconiine butterfly via gas chromatography/electroantennography revealed an unprecedented active compound. The males transfer this compound to females during mating. The structure of (2,6,10)-2,6-dimethyl-6-undecen-10-olide, a derivative of geranylacetone, was proposed on the basis of infrared and mass spectrometry spectra and microderivatization and confirmed by racemic and stereoselective syntheses.