| Title: | Synthesis and biological activity of the four stereoisomers of 4-methyl-3-heptanol: main component of the aggregation pheromone of Scolytus amygdali |
| Author(s): | Zada A; Ben-Yehuda S; Dunkelblum E; Harel M; Assael F; Mendel Z; |
| Address: | "Institute of Plant Protection, Volcani Center, Bet Dagan, 50250, Israel. anatzada@volcani.agri.gov.il" |
| DOI: | 10.1023/b:joec.0000018634.94866.5b |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| 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" |
| Keywords: | "Animals Coleoptera/*metabolism/physiology Female Heptanol/*analogs & derivatives/*metabolism Male Molecular Structure Pheromones/*chemical synthesis/chemistry/pharmacology Sexual Behavior, Animal/drug effects/physiology Stereoisomerism Structure-Activity;" |
| Notes: | "MedlineZada, A Ben-Yehuda, S Dunkelblum, E Harel, M Assael, F Mendel, Z eng Comparative Study Research Support, Non-U.S. Gov't 2004/05/14 J Chem Ecol. 2004 Mar; 30(3):631-41. doi: 10.1023/b:joec.0000018634.94866.5b" |
