Recent results in the synthesis of ecologically important bioregulators*
Kenji Mori
Department of Chemistry, Faculty of Science, Science
University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan
Abstract: Absolute configuration was established for the following
semiochemicals: (S)-polyzonimine (1), (S)-9-methylgermacrene-B (2) and
(1S,3S,7R)-3-methyl-a-himachalene (3). The stereoisomers of 2,6-dimethylheptane-1,7-diol
monotetrahydropyranyl ether served as useful building blocks for the
synthesis of syn- or anti-1,5-dimethylated aliphatic pheromones such
as 4 and 5. Synthesis of analogs of the Israeli pine bast scale pheromone
6, which exhibits both pheromonal and kairomonal activities, enabled
us to find a strong pheromone mimic 7 without any kairomonal activity.
*Lecture presented at the 22nd IUPAC International
Symposium on the Chemistry of Natural Products, São Carlos, Brazil,
3-8 September 2000. Other presentations are published in this issue,
pp. 549-626.
