Absolute configuration of anabasine from Messor and Aphaenogaster ants

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.