para-Menthane-(3,8)-diol (PMD), a compound produced by the lemon eucalyptus tree, is a mosquito repellent whose potency is partially attributable to its low volatility. PMD is one of a small number of natural products approved by the Center for Disease Control as a mosquito repellent. Using the terpenoid skeleton of PMD as a scaffold, a library of compounds, varying in the degree of oxygenation, polarity and, inter alia volatility, was synthesized. (-)-Citronellal was converted to isopulegol. To-date, the double bond of citronellal has been functionalized by hydroboration and dihydroxylation. The synthesis of other analogs is in progress. Following synthesis and characterization, the compounds will be tested in assays to determine their mosquito repellancy.

Modifications to para-menthane-(3,8)-diol to increase mosquito repellency

255th National Meeting (2018)

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