W. Francke et al., SYNTHESIS OF -ETHYL-1,5-DIMETHYL-6,8-DIOXABICYCLO[3.2.1]OCTANE, THE AGGREGATION PHEROMONE OF MALE BEECH BARK BEETLES, TAPHRORYCHUS BICOLOR (COL, SCOL), Liebigs Annalen, (10), 1996, pp. 1523-1527
The absolute configuration of the new bicyclic acetal 2-ethyl-1,5-dime
thyl-6,8-dioxabicyclo[3.2.1]octane (1), identified as an aggregation p
heromone of males of the beech bark beetle, Taphrorychus bicolor, was
determined by unambiguous synthesis and NMR experiments. The syntheses
of the racemates of both diastereomers and of optically pure samples
are described. The natural product proved to show (1S,2R,5R) configura
tion.