Total synthesis, proof of absolute configuration, and biosynthetic origin of stylopsal, the first isolated sex pheromone of strepsiptera.

@article{Lagoutte2013TotalSP,
  title={Total synthesis, proof of absolute configuration, and biosynthetic origin of stylopsal, the first isolated sex pheromone of strepsiptera.},
  author={Roman Lagoutte and Petr {\vS}ebesta and Pavel Jiro{\vs} and Blanka Kalinov{\'a} and Anna Jiro{\vs}ov{\'a} and Jakub Straka and Kateřina Amruz {\vC}ern{\'a} and Jan {\vS}obotn{\'i}k and Josef Cva{\vc}ka and Ullrich Jahn},
  journal={Chemistry},
  year={2013},
  volume={19 26},
  pages={
          8515-24
        }
}
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 α,β-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The… 
Total Synthesis, Stereochemical Assignment, and Field-Testing of the Sex Pheromone of the Strepsipteran Xenos peckii.
TLDR
Strong field trapping data, in combination with spectroscopic and chiral GC data, unambiguously demonstrate that (3R,5S,9R,7E,11E)-3,5,9, 11-tetramethyl-7,11-tridecadienal is the X. peckii sex pheromone.
(7E,11E)-3,5,9,11-Tetramethyltridecadienal: Sex Pheromone of the Strepsipteran Xenos peckii
TLDR
A candidate pheromone component (CPC) was identified as (7E,11E)-3,5,9,11-tetramethyltridecadienal based on its retention indices on three GC-columns, RI inter-column differentials, mass and NMR spectra, and synthesis of an authentic standard that matched the GC-retention and spectrometric characteristics of the CPC.
Chiral methyl-branched pheromones.
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While this review deals only with chiral methyl-branched pheromones, the chemical structures of more than one hundred non-terpene compounds have been determined by applying excellent analytical techniques and by employing trustworthy chiral sources and ingenious enantioselective reactions.
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TLDR
It is concluded that Strepsiptera fall within the synchronous sensory exploitation model where short-lived males take advantage of a pre-existing sensory system involving pheromone signals emitted by females.
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An efficient copper-catalyzed enantioselective conjugate addition of dimethylzinc to unsaturated 2-acyl-N-methylimidazoles has been achieved using a chiral bidentate hydroxyalkyl-NHC ligand. The
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TLDR
It is postulate that the original mode of traumatic insemination was maintained after the transition from free-living to endoparasitic strepsipteran females, and a novel paragenital organ of Stylops females, the cephalothoracic invagination, is described to reduce the cost of injuries.
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