Synthesis and Enantioselective Gas Chromatography of Stereoisomers of 7,11-Dimethylheptadecane− A Pheromone Component ofLambdina Species

Abstract The stereoisomers of 7,11‐dimethylheptadecane exhibit a useful level of separation under enantioselective gas chromatographic conditions, using a modified cyclodextrin phase. Synthesis of the (7 R ,11 R ) isomer and coinjection studies establish the order of elution as (7 S ,11 S ), (7 R ,11 R ), and finally the meso form, the latter being a sex‐pheromone component of Lambdina species. Enantiomeric assays of natural samples containing this hydrocarbon system will now be possible. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)