Absolute configuration of anabasine from Messor and Aphaenogaster ants

A method has been developed to assign the absolute configuration and enantiomeric excess of anabasine based on small amounts of material (in the microgram range), by derivatization with (+)-menthylchloroformate followed by capillary 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 Aphaenogaster subterranea and A. miamiana (2'S)-anabasine was determined to have an ee of 78 and 24%, respectively.