K. Domon et K. Mori, Pheromone synthesis, CXCIII Simple synthesis of (+/-)-stigmolone (8-hydroxy-2,5,8-trimethyl-4-nonanone), the pheromone of Stigmatella aurantiaca, EUR J ORG C, (5), 1999, pp. 979-980
The racemic myxobacterial pheromone (+/-)-1 (stigmolone), which induces the
formation of the fruiting body of Stigmatella aurantiaca, was synthesized
from methyl isobutyl ketone (2) in 48% overall yield in four steps.