Use of the Anti-Oxidant Butylated Hydroxytoluene in situ for the Synthesis of Readily Oxidized Compounds: Application to the Synthesis of the Moth Pheromone (Z,Z,Z)-3,6,9-Nonadecatriene

The triene (Z,Z,Z)-3,6,9-nonadecatriene was synthesized in three steps from methyl linolenate. The key to the synthesis was the use of the anti-oxidant butylated hydroxytoluene in situ to provide protection of the unstable triene from autoxidation during reaction workup. This simple modification resulted in an increase in the yield from 20 to 85% over three steps. © CSIRO 2007.