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Synthesis and Enantioselective Gas Chromatography of Stereoisomers of 7,11‐Dimethylheptadecane − A Pheromone Component of Lambdina Species
Author(s) -
Chow Sharon,
Koenig Wilfried A.,
Kitching William
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300643
Subject(s) - enantioselective synthesis , chemistry , enantiomer , elution , pheromone , component (thermodynamics) , gas chromatography , stereochemistry , chromatography , hydrocarbon , organic chemistry , catalysis , physics , thermodynamics , biology , genetics
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)