Synthesis of the male stable fly polyene (Z,Z)-1,7,13-pentacosatriene and its geometrical isomers
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The four geometrical isomers of 1,7,13-pentacosatriene were synthesized from 1,7-octadiyne. Two of the required isomers were synthesized using known methodology. Hydrogenation of acetylenic linkages were employed to produce predominantly cis alkenes, and alkali metal/amine reduction was used to produce a trans alkene. It was thus possible to produce the (Z,Z) and the (Z,E) isomers. Methods for olefin inversion were then employed to obtain the other two isomers.
Key wordsStable fly Stomoxys calcitrans (L.) pheromone sex pheromone polyene mating stimulant (Z,Z)-1,7,13-pentacosatriene
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