NMR SPECTRAL ASSIGNMENT OF LACTONE PHEROMONE COMPONENTS EMITTED BY CARIBBEAN AND MEXICAN FRUIT-FLIES

By utilizing one- and two-dimensional nuclear magnetic resonance techniques, the complete assignments of the proton and carbon spectra of the lactones anastrephin, epianastrephin, and suspensolide have been accomplished. These compounds are pheromone components for both the Caribbean and Mexican fruit flies. The relative stereochemistries of anastrephin and epianastrephin were demonstrated by nuclear Overhauser difference spectroscopy. With complete spectral assignments now available, biosynthesis of these molecules may be studied by feeding specific isotopically labeled nutrients to flies and subsequently analyzing the volatiles produced for the presence and position of the labelling isotope.