Abstract
Stereoisomers of 4-methyl-3-heptanol are major components of aggregation pheromones of bark beetles and trail pheromones of ants. Recently, (3S,4S)-4-methyl-3-heptanol (I) has been tentatively identified as the main component of the aggregation pheromone of the almond bark beetle, Scolytus amygdali (Coleoptera: Scolytidae). The four stereoisomers of 4-methyl-3-heptanol were prepared and bioassayed. Key steps included preparation of chiral 4-methyl-3-heptanones using SAMP and RAMP reagents, reduction to the corresponding alcohols, and stereospecific transesterification with vinyl acetate with lipase AK catalysis. In field tests, only (3S,4S)-4-methyl-3-heptanol attracted beetles in combination with the synergist (3S,4S)-4-methyl-3-hexanol, whereas (3R,4S)- and (3R,4R)-4-methyl-3-heptanols were inhibitory.
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Zada, A., Ben-Yehuda, S., Dunkelblum, E. et al. Synthesis and Biological Activity of the Four Stereoisomers of 4-Methyl-3-Heptanol: Main Component of the Aggregation Pheromone of Scolytus amygdali . J Chem Ecol 30, 631–641 (2004). https://doi.org/10.1023/B:JOEC.0000018634.94866.5b
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DOI: https://doi.org/10.1023/B:JOEC.0000018634.94866.5b