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

Abstract

A straightforward stereospecific synthesis of two stereoisomers, (4R, 8S) and (45, 8S), of 4,8-dimethyldecanal (1), out of four possible isomers, is described. The key step employs the coupling reaction of tosylates (3) and (3a), which are obtained from (R)- and (S)- citronellol, with the chiral Grignard reagent prepared from comercial (S)-(+)-1-bromo-2-methylbutane (4).