Abstract
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.
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Sonnet, P.E. Synthesis of the male stable fly polyene (Z,Z)-1,7,13-pentacosatriene and its geometrical isomers. J Chem Ecol 5, 415–422 (1979). https://doi.org/10.1007/BF00987926
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DOI: https://doi.org/10.1007/BF00987926