Submitted to: European Journal of Organic Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/18/2001
Publication Date: N/A
Interpretive Summary: Tsetse flies are vectors of a fatal and debilitating disease called Nagana in domestic animals in Africa, which has been known as sleeping sickness in humans. The International Atomic Energy Agency, often called the IAEA, has sponsored work at locations around the world to help combat this dangerous pest. A scientist at the USA laboratory in Gainesville was asked by the IAEA to help identify the sex pheromone of one of the important species of tsetse fly in East Africa coastal areas called Glossina austeni. His previous study identified the two most likely candidate compounds. The present work involved synthesis of eight variations of these two compounds, then confirming the identity of the man-made compound using a modern technique called mass spectrometry.
Technical Abstract: All of the stereoisomers of 13,17-dimethyl-1-tritriacontene (1) and 13,17-dimethyl-1-pentatriacontene (2), the contact sex pheromone components of the female tstse fly (Glossina austeni), were synthesized starting from the enantiomers of the protected syn- and anti-2,6-dimethylheptane-1,7-diol (3), which were prepared from the enantiomers of methyl 3-hydroxy-2-methylpropanoate (4) and methyl phenyl sulfone (5).