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

  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},
  volume={19 26},
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.
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
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.
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.
Stereocontrolled Total Synthesis of (−)‐Stemaphylline
The methodology was used in the total synthesis of the Stemona alkaloid (−)‐stemaphylline in just 11 steps (longest linear sequence), with high stereocontrol (>20:1 d.r.) and 11 % overall yield.
Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium.
Five of the seven compounds isolated were determined to be 2-alkylquinolin-4(1H)-ones with varying side chains and were synthesized to confirm their structure as a new antiplasmodial compound.
We do not select, nor are we choosy: reproductive biology of Strepsiptera (Insecta)
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.
Copper‐Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl‐N‐methylimidazole Michael Acceptors: Scope, Limitations and Iterative Reactions
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
Review of the Biology of Parasitic Insects in the Order Strepsiptera
Members of the Strepsiptera exhibit pronounced sexual dimorphism, 2 distinct larval forms, a pupal stage, host manipulation, and morphological characteristics that include many unusual differences from other insects.
Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination
The Wittig olefination utilizing phosphoranes and the related Horner-WadsworthEmmons (HWE) reaction using phosphonates transform aldehydes and ketones into substituted alkenes. Because of the
Traumatic insemination and female counter-adaptation in Strepsiptera (Insecta)
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.


Asymmetric Total Synthesis of Callystatin A: Asymmetric Aldol Additions with Titanium Enolates of Acyloxazolidinethiones
A number of highly cytotoxic polyketides, including the anguinomycins,1 leptofuranins,2 leptomycin,3 and kazusamycin,4 having similar gross chemical structures have been isolated from Streptomyces
Stylopsal: The First Identified Female-produced Sex Pheromone of Strepsiptera
A female-produced sex pheromone of Stylops muelleri was identified as an unusually branched saturated aldehyde (9R)-3, 5-syn-3,5,9-trimethyldodecanal, which gave identical chromatographic and mass spectrometric data as the natural phersomone and also was active in electroantennographic and behavioral assays.
Total Synthesis of (−)-Ircinianin and (+)-Wistarin†
(−)-Ircinianin (1), a cyclic furanosesterterpenetetronic acid isolated from a marine sponge (genus Ircinia), is synthesized in 17 steps from (S)-2-methylpropane-1,3-diol mono THP ether 10 and
First Sex Pheromone of the Order Strepsiptera: (3R,5R,9R)-3,5,9-Trimethyldodecanal in Stylops melittae Kirby, 1802
The first identification and synthesis of a female-produced strepsipteran sex pheromone, (3R,5R,9R)-3,5,9-trimethyldodecanal, from Stylops melittae, a species parasitizing andrenid bees is reported.
Pheromone Synthesis, CLXVII. Synthesis of All of the Eight Stereoisomers of Methyl 2,6,10-Trimethyltridecanoate, the Male-Produced Pheromone of the Stink Bugs, Euschistus heros and E. obscurus
All of the eight possible stereoisomers of methyl 2,6,10-trimethyltridecanoate (1), the male-produced attractant pheromone of the South American soybean pest, Euschistus heros, and that of E.
Bioactive natural products and chirality.
  • K. Mori
  • Chemistry, Medicine
  • 2011
Results indicate that bioactive natural products are not always enantiomerically pure, and the stereochemistry-bioactivity relationships are not simple but complicated.
Total syntheses of amphidinolides B1, B4, G1, H1 and structure revision of amphidinolide H2.
A robust, convergent and hence general blueprint is described which allowed not only to conquest five prototype members of these series, but also holds the promise of making "non-natural" analogues available by diverted total synthesis.
Sex Pheromone of the Pine Sawfly Macrodiprion nemoralis (Hymenoptera : Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecanol as the Precursor for the Active Pheromone Acetate
Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.
New Amino Endoperoxides Belonging to the Antimalarial G‐Factor Series
In the search for new antimalarial endoperoxides we developed a direct route for the preparation of new amino compounds belonging to the G-factor series. During the synthesis, a significant
The Sex Pheromone of the Pine Sawfly Microdiprion pallipes (Hymenoptera: Diprionidae)
Correspondence to: H.-E. Hogberg, e-mail: The pheromone of the pine sawfly Microdiprion pallipes (Fallen) (Hymenoptera: Diprionidae) has been identified as at least one