Entomology, Department of


Date of this Version

February 2004


Published in Eur. J. Org. Chem. 2004, 1089-1096.


Starting from the enantiomers of citronellal and 1-octyn-3- ol, all four stereoisomers of 6-acetoxy-19-methylnonacosane were synthesized with sufficiently high stereochemical purities (more than 90% ee at C-6; about 97% ee at C-19) for their biological testing as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax). All four isomers showed strong pheromone activity even at 1 μg, and no significant difference was observed in their potency. Adams’ platinum oxide was found to cause partial racemization of enantiomerically pure secondary propargylic alcohols in the course of their catalytic hydrogenation to saturated and secondary alcohols, while palladium-charcoal was less potent in causing partial racemization. A new HPLC-based discrimination of chiral and secondary alcohols proved to be useful in following such a subtle partial racemization.

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