Stereospecific synthesis of two isomers of (4,8)-dimethyldecanal: The aggregation pheromone of Tribolium spp

A straightforward stereospecific synthesis of two stereoisomers, (4R, 8S) a nd (4S, 8S), of 4,8-dimethyldecanal (1), out of four possible isomers, is d escribed. The key step employs the coupling reaction of tosylates (3) and ( 3a), which are obtained from (R)- and (S)- citronellol, with the chiral Gri gnard reagent prepared from comercial (S)-(+)1-bromo-2-methylbutane (4).