Synthesis of 2,4-Dimethyl-5-hexanolide, 2,4-Dimethyl-5-heptanolide and 2,4-Dimethyl-5-octanolide, the Lactones Identified in Volatiles from the Heads of the Male Black Garden Ant, Lasius niger

Abstract

2,4-Dimethyl-5-hexanolide (1), 2,4-dimethyl-5-heptanolide (2), and 2,4-dimethyl-5-octanolide (3) are the volatile substances identified in the heads of the male black garden ant, Lasius niger. (2R,4R,5S)-Isomers of these lactones were synthesized by employing the iodolactonization reaction (5→4) as the key step.