Peterson, John Robert
M.S. (Master of Science)
Department of Chemistry
Heterocyclic compounds; Insect sex attractants
Insect pheromones are compounds of Interesting biological activity. Using readily available starting materials, an efficient synthesis was developed for a sex pheromone Isolated from the male swift moth ti£B.l.ga,lug he eta L. A new entry into substituted 2,3-dihydro-4H- pyran-4-ones using titanium tetrachloride and bls(si1y1enolJethers is presented. These heterocyclic frameworks are common to many natural products. A model synthesis of the insect pheromone was explored with other routes investigated from the results. Strategies for optimization of the dlastereo- merlc selectivity In the formation of 4H-pyran-4-ones is discussed. The optimization of this diastereomeric relationship was considered an Important step towards the synthesis of the natural pheromone. Finally, an efficient total synthesis of this insect pheromone is presented.
Kirchhoff, Eric W., "Synthesis of 1,8-dimethyl-e-exo-ethyl-2,9-dioxabicyclo[3.3.1]non-7-ene by Eric W. Kirchoff" (1989). Graduate Research Theses & Dissertations. 5185.
v, 68 pages
Northern Illinois University
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