Pheromone synthesis, CXCI - Synthesis of the enantiomers of 8-hydroxy-2,5,8-trimethyl-4-nonanone, the myxobacterial pheromone of Stigmatella aurantiaca to induce the formation of its fruiting body

The enantiomers of the title compound 1 were synthesized from the enantiomers of citronellol (2). Both (R)- and (S)-1 induced the formation of the fruiting body of a myxo-bacterium Stigmatella aurantiaca at a concentration of 0.4-1.0 nM.