Synthesis and biological activity of the four stereoisomers of 4-methyl-3-heptanol: main component of the aggregation pheromone of Scolytus amygdali.
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.
Zada
A
A
Institute of Plant Protection, Volcani Center, Bet Dagan, 50250, Israel. anatzada@volcani.agri.gov.il
Ben-Yehuda
S
S
Dunkelblum
E
E
Harel
M
M
Assael
F
F
Mendel
Z
Z
D000818:Animals; D001517:Coleoptera / Q000378:metabolism* / Q000502:physiology; D005260:Female; D019850:Heptanol / Q000031:analogs & derivatives* / Q000378:metabolism*; D008297:Male; D015394:Molecular Structure; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012726:Sexual Behavior, Animal / Q000187:drug effects / Q000502:physiology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D010675:Pheromones; D019850:Heptanol