Recent results in the synthesis of ecologically important bioregulators

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.