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Statements

Subject Item
n2:RIV%2F60460709%3A41320%2F13%3A60377%21RIV14-MSM-41320___
rdf:type
skos:Concept n8:Vysledek
dcterms:description
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 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
dcterms:title
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
skos:prefLabel
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
skos:notation
RIV/60460709:41320/13:60377!RIV14-MSM-41320___
n8:predkladatel
n9:orjk%3A41320
n3:aktivita
n16:I n16:S n16:P
n3:aktivity
I, P(GAP506/10/1466), S
n3:cisloPeriodika
26
n3:dodaniDat
n12:2014
n3:domaciTvurceVysledku
n18:7372329
n3:druhVysledku
n15:J
n3:duvernostUdaju
n10:S
n3:entitaPredkladatele
n17:predkladatel
n3:idSjednocenehoVysledku
111314
n3:idVysledku
RIV/60460709:41320/13:60377
n3:jazykVysledku
n4:eng
n3:klicovaSlova
asymmetric synthesis, configuration determination, pheromones, total synthesis, Wittig reactions
n3:klicoveSlovo
n5:Wittig%20reactions n5:asymmetric%20synthesis n5:configuration%20determination n5:pheromones n5:total%20synthesis
n3:kodStatuVydavatele
CZ - Česká republika
n3:kontrolniKodProRIV
[B90F87CF977E]
n3:nazevZdroje
CHEMISTRY-A EUROPEAN JOURNAL
n3:obor
n14:CC
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
10
n3:projekt
n13:GAP506%2F10%2F1466
n3:rokUplatneniVysledku
n12:2013
n3:svazekPeriodika
19
n3:tvurceVysledku
Cvačka, Josef Jahn, Ullrich Lagoutte, Roman Šobotník, Jan Straka, Jakub Černá, Kateřina Šebesta, Petr Kalinová, Blanka Jiroš, Pavel Jirošová, Anna
n3:wos
000320390500021
s:issn
0947-6539
s:numberOfPages
10
n19:organizacniJednotka
41320