Abstract
Bicyclic acetals play an important role as volatile signals in systems of chemical communication among many insect species, i.e. bark beetles, weevils, and moths. They represent cryptic ketodiols with a glycol- and 1,3- diol-substructure. Alkylated members of four different systems are known, namely derivatives of 2,7-dioxabicyclo[2.2.1]heptane, 2,8-dioxabicyclo [3.2.1]octane, 6,8-dioxabicyclo[3.2.1]octane, and 2,9-dioxabicyclo[3.3.1] nonane. Some of the compounds carry an additional oxygen function. A couple of structures have been extensively used as model compounds for studies in synthetic organic chemistry. Brevicomin, 7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane as well as frontalin, 1,5-dimethyl- 6,8-dioxabicyclo[3.2.1]octane, have been most frequently prepared. Both pheromones are components of a kind of dialog between males and females of Dendroctonus bark beetles. Also, predators use them as kairomones. Frontalin and 1,3,3-trimethyl-2,7- dioxabicyclo[2.2.1]heptane have been found in volatiles of elephants and men, respectively, however, their biological significance is unknown in these cases. This review will provide an overview over structures of bicyclic acetals which are used as pheromones. It will comprise present knowledge on their occurrence and biological function and include facts and speculations concerning their biosynthesis. Furtheron, analytical aspects, especially mass spectrometry will be discussed, and plotted spectra will be shown. Syntheses, especially those providing optically active products carried out during the last eight years, will be reviewed.
Call for Papers in Thematic Issues
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