Semiochemicals of the Scarabaeinae
作者： B.V. Burger , W.G.B. Petersen , B.T. Ewig , J. Neuhaus , G.D. Tribe
DOI: 10.1016/J.CHROMA.2007.09.041
关键词:
摘要: Using gas chromatography with flame ionization detection and electroantennographic in parallel (GC-FID/EAD), the active constituents of sex attractant male dung beetles Kheper bonellii were located chromatogram an extract secretion. These identified as propanoic acid, butanoic indole, 3-methylindole (skatole) methyl cis-cascarillate (methyl cis-2-2′-hexylcyclopropylacetate) by, inter alia, GC–MS, 1H 13C NMR analysis, synthesis. compounds elicited EAD responses well female antennae. Racemic was synthesized for comparison natural ester. Enantioselective GC-FID/EAD using a capillary column coated OV-1701-OH containing 10% heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin showed that compound co-eluted first-eluting enantiomer racemic cis-cascarillate, which only antennae K. bonellii. The absolute configuration this established by stereoselective synthesis, gave (R,R)-cascarillate [methyl (1′R,2′R)-2-2′-hexylcyclopropylacetate] enantiomeric excess 69%.
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