Identification and Stereoselective Total Synthesis of an Insect Homosesquiterpene from the Clonal Raider Ant Ooceraea biroi

Ants typically demonstrate a high level of complex social behavior that is largely mediated by chemical communication. In recent years, the Clonal raider ant Ooceraea biroi has become a promising model system for the study of social behavior in ants. Here we report the profile of extracted volatiles from O. biroi and, following detection of an α-homofarnesene as the major component, unambiguously confirm its structural identity as (3Z,6E)-14-methyl-α-farnesene through preparative stereoselective total synthesis.