A method has been developed to assign the absolute configuration and enanti
omeric excess of anabasine based on small amounts of material (in the micro
gram range), by derivatization with (+)-menthylchloroformate followed by ca
pillary GC analysis of the resulting carbamate(s). This method was applied
to three samples of anabasine isolated from Messor and Aphaenogaster ants.
In Messor sanctus, only (2'S)-anabasine was present, whereas in Aphaenogast
er subterranea and A. miamiana (2'S)-anabasine was determined to have an ee
of 78 and 24%, respectively.