Abstract
A synthesis of (Z,Z)-11,13-hexadecadienal, a compound previously identified as the major component of the sex pheromone of the female navel orangeworm,Amyelois transitella (Walker), is described. The key step is the reduction of an unsymmetrical conjugated diyne with dicyclohexylborane. This reduction produced theZ,Z isomer with less than 0.5% total of other isomers.
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Sonnet, P.E., Heath, R.R. Stereospecific synthesis of (Z,Z)-11,13-hexadecadienal, a female sex pheromone of the navel orangeworm,Amyelois transitella (Lepidoptera: Pyralidae). J Chem Ecol 6, 221–228 (1980). https://doi.org/10.1007/BF00987541
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DOI: https://doi.org/10.1007/BF00987541