Abstract: The first total synthesis of the sex pheromone of the oleander scale Aspidiotus nerii (5), an economically important polyphagous pest, is described. The synthesis is based on a stereocontrolled and completely regioselective intramolecular exo-cyclization of cis- epoxynitrile 9 to afford cyclobutane alcohol t-10 stereoselectively. Introduction of the unusual 4-methylpent-4-enyl group onto the cyclobutane skeleton was effected through Wittig ...
