Rapid configuration analysis of the solenopsins

A protocol for rapid access to the relative and absolute configurations of the solenopsins, the venom alkaloids of fire ants (Solenopsis spp.), was developed based on chiral capillary gas chromatography. The synthesis of racemic mixtures of 2-methyl-6-alkylpiperidines and the isolation of natural (2R,6R)- and (2R,6S)-2-methyl-6-undecylpiperidines allowed for the standardization of the chromatographic method. Application of this protocol revealed the previously unknown natural occurrence of four stereoisomers of 2-methyl-6-undecylpiperidine in venom samples from workers and gynes of Solenopsis saevissima.

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C17H36NCl(2R,6S)-2-Methyl-6-undecylpiperidine hydrochloride[α]D20=+7 (c 0.6, CHCl3)Absolute configuration: (2R,6S)

C17H36NCl(2R,6R)-2-Methyl-6-undecylpiperidine hydrochloride[α]D20=-4 (c 0.67, CHCl3)Absolute configuration: (2R,6R)