. "CHEMISTRY-A EUROPEAN JOURNAL" . . "0947-6539" . "asymmetric synthesis, configuration determination, pheromones, total synthesis, Wittig reactions"@en . "Cva\u010Dka, Josef" . . "[B90F87CF977E]" . "Jahn, Ullrich" . "I, P(GAP506/10/1466), S" . "Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera"@en . "RIV/60460709:41320/13:60377!RIV14-MSM-41320___" . . "000320390500021" . "19" . "111314" . . "Lagoutte, Roman" . . "The asymmetric total synthesis of the diastereomers of stylopsal establishes the absolute configuration of the first reported sex pheromone of the twisted-wing parasite Stylops muelleri as (3R,5R,9R)-trimethyldodecanal. The key steps for the diastereo- and enantiodivergent introduction of the methyl groups are two different types of asymmetric conjugate addition reactions of organocopper reagents to alpha,beta-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The structure of the natural product was confirmed by chiral gas chromatography (GC) techniques, GC/MS and GC/electroantennography (EAD) as well as field tests. An investigation into the biosynthesis of the pheromone revealed that it is likely to be produced by decarboxylation of a 4,6,10-trimethyltridecanoic acid derivative, which was found in substantial amounts in the fat body of the female, but not in the host bee Andrena vaga. This triple-branched fatty acid precursor thus seems to be biosynthesized de nov" . "RIV/60460709:41320/13:60377" . . . "CZ - \u010Cesk\u00E1 republika" . . . "1"^^ . . . "10"^^ . "Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera" . . "\u0160obotn\u00EDk, Jan" . "Straka, Jakub" . . "Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera" . . . "Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera"@en . . . "\u010Cern\u00E1, Kate\u0159ina" . "\u0160ebesta, Petr" . "Kalinov\u00E1, Blanka" . . "The asymmetric total synthesis of the diastereomers of stylopsal establishes the absolute configuration of the first reported sex pheromone of the twisted-wing parasite Stylops muelleri as (3R,5R,9R)-trimethyldodecanal. The key steps for the diastereo- and enantiodivergent introduction of the methyl groups are two different types of asymmetric conjugate addition reactions of organocopper reagents to alpha,beta-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The structure of the natural product was confirmed by chiral gas chromatography (GC) techniques, GC/MS and GC/electroantennography (EAD) as well as field tests. An investigation into the biosynthesis of the pheromone revealed that it is likely to be produced by decarboxylation of a 4,6,10-trimethyltridecanoic acid derivative, which was found in substantial amounts in the fat body of the female, but not in the host bee Andrena vaga. This triple-branched fatty acid precursor thus seems to be biosynthesized de nov"@en . "Jiro\u0161, Pavel" . . "26" . "10"^^ . "Jiro\u0161ov\u00E1, Anna" . "41320" .