| Three insect species sex or aggregation pheromones have been studied. A new aggregation pheromone component, lanierone, (2-hydroxyl-4,4,6-tri-methyl-2,5-cyclohexadiene-1-one) was isolated and identified from a Porapak Q collection of volatiles from male bark beetle, Ips pini from New York through GC fractionation, bioassay, and spectrometry. The postulated structure was confirmed by synthesis. A proposed structure of the sex pheromone component, matsuone, (2E, 4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one) obtained from the pine bast scales, Matsucoccus resinosae from the United States, M. matsumurae from China, and M. thunbergianae from Korea has been confirmed by synthesis requiring 18 steps. A coupling reaction is the key step in this synthetic pathway. A new sex pheromone component, supellanone, (5-(2,4-dimethylheptanyl)-3-methyl-2H-pyran-2-one) was isolated and identified from hexane extracts of abdominal tergites from female brown-banded cockroach, Supella longipalpa using the same strategies described for lanierone. The new sex pheromone component supellanone and three analogs have been synthesized. A practical methodology for the construction of 3,5 disubstituted 2H-pyran-2-one has been developed. The new synthetic method which permits an entrance to this unique class of compounds has been reported in this thesis. |
