Abstract
Integrated pest management (IPM) is an area of agriculture research secondary to the negative impacts of conventional pesticides. Pheromones have been shown to be effective approaches in pest control with minimal risk to humans and the environment. We describe projects that contribute to pheromone research. Firstly, we describe a method for synthesis of the pheromone exo-brevicomin (7-ethyl-5-methyl- 6,8-dioxabicyclo[3.2.1]octane) using tosylation of alcohol followed by alkylation and cyclization. This stereoselective method is unique compared to others. Secondly, we describe a method for the oxidation of primary alcohols to aldehyde using trichloroisocyanuric acid and 2,2,6,6-tetramethyl-1-pipredinyloxy in the presence of sodium bicarbonate or p-tolunesulfonic acid. Also described is the direct conversion of a primary alcohol to alpha-chloroaldehyde. This has future potential in pheromone research. Finally, we explored conditions for a cost-effective and efficient direct mixed Claisen condensation using LDA as base to yield ketoesters that can then be converted to ketones. The Claisen condensation can be used to further synthesize the pheromone 7-Methyl-l,6- dioxaspiro[4.5]decane.. This method is more efficient and potentially more cost-effective than other previously described methods.