Pheromones of Coleoptera. 12. Synthesis of (+/-)-2,6-dimethyloctyl formate, the biologically active analog of the smaller flour beetle aggregation pheromone

Article abstract of DOI:10.1007/BF00704018

Racemic 2,6-dimethyloctyl formate (1), a synthetic analog of the aggregation pheromone of two species of Tribolium beetles, has been obtained in six steps and in 28 percent overall yield starting from methyl ethyl ketone, vinyl bromide, and 2-methylpropenal.The key step of the synthesis is the sigmatropic <3,3>-rearrangement of 4-ethyl-2,4-dimethyl-1,5-hexadien-3-ol (5) to 2,6-dimethyl-5-octenal (6).