Positions and Stereochemistry of Methyl Branches in the Novel Sex Pheromone Components Produced by a Lichen Moth, Lyclene dharma dharma

@article{Adachi2010PositionsAS,
  title={Positions and Stereochemistry of Methyl Branches in the Novel Sex Pheromone Components Produced by a Lichen Moth, Lyclene dharma dharma},
  author={Yasushi Adachi and Nguyen Duc Do and Masakatsu Kinjo and Saori Makisako and Rei Yamakawa and Kenji. Mori and Tetsu Ando},
  journal={Journal of Chemical Ecology},
  year={2010},
  volume={36},
  pages={814-823}
}
Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce three sex pheromone components (I–III), for which we assigned the following novel chemical structures; 6-methyl-2-octadecanone (1) for I, 14-methyl-2-octadecanone (2) for II, and 6,14-dimethyl-2-octadecanone (3) for III. In the Iriomote Islands where the insects were collected, a lure including racemic 1 and 2 attracted the male moths without mixing 3. In this study for further confirmation of the plane structures, the… 
Synthesis and Field Evaluation of Stereoisomers and Analogues of 5-Methylheptadecan-7-ol, an Unusual Sex Pheromone Component of the Lichen Moth, Miltochrista calamina
TLDR
Females of the lichen moth, Miltochrista calamina, were previously shown to produce 5-methylheptadecan-7-ol as a sex pheromone, but males were attracted only by the (5R,7R)-isomer of the four stereoisomers that were prepared by separation from two mixtures of diastereoisomers.
Synthesis of Four Stereoisomers of (S)‐2‐Methylpent‐3‐yl 3,13‐Dimethylpentadecanoate, a Sex Pheromone of the Bagworm Moth Clania variegate, Using Stereospecific Inversion of Secondary Sulfonates as a Key Step
Females of some lepidopteran species produce novel sex pheromones with a methyl-branched structure, such as 2-methylpent-3-yl 3,13-dimethylpentadecanoate secreted by the bagworm moth Clania
Propionates and Acetates of Chiral Secondary Alcohols: Novel Sex Pheromone Components Produced by a Lichen Moth Barsine expressa (Arctiidae: Lithosiinae)
TLDR
Females of a lichen moth, Barsine expressa, which inhabit Iriomote Island in Japan, were captured by a black-light trap and the pheromone gland extract was analyzed, showing a straight-chain structure of the C17 alcohols with the acyl groups located at the 7- or 8-position.
Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6,14-Dimethyl-2-octadecanone, Sex Pheromone Components of the Lyclene dharma dharma Moth, from the Enantiomers of Citronellal
TLDR
Three well-established procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.
Identification of Sex Pheromone of Miltochrista striata (Lepidoptera: Arctiidae).
TLDR
The results represent the first determination of the sex pheromone of a lichen moth in a tea plantation and provide a scientific basis to develop an effective protocol using sex phersomone to monitor populations of M. striata.
Identification of the Sex Pheromone of Female Eurata patagiata1
TLDR
Behavioral assays showed that more than 90% of male moths were attracted to a mixture of the pheromones rather than to hexane, however, the percentage decreased when only one compound was assayed.
...
...

References

SHOWING 1-10 OF 29 REFERENCES
Synthesis and Field Evaluation of Methyl-branched Ketones, Sex Pheromone Components Produced by Lithosiinae Female Moths in the Family of Arctiidae
TLDR
Female moths of Lyclene dharma dharma produce a novel sex pheromone composed of three methyl-branched ketones, and effective male attraction was observed for the 2:1:1 mixture of I–III, indicating that the females do not produce only one stereoisomer for each component or that the response of the males is not disturbed by the other stereoisomers of natural isomers produced by the females.
Improved Synthesis of Three Methyl-Branched Pheromone Components Produced by the Female Lichen Moth
TLDR
Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce a novel sex pheromone composed of three methyl-branched ketones, which were confirmed by syntheses accomplished by a different route for each component.
A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae
TLDR
Female moths of Lyclene dharma dharma produced three pheromone components (I–III), which strongly stimulated male antennae, indicating that these methyl-branched ketones constitute a new chemical group of lepidopteran female sex phersomones.
Synthesis of the Deuterated Sex Pheromone Components of the Grape Borer, Xylotrechus pyrrhoderus
TLDR
Deuterated derivatives of both components were synthesized by starting from a Wittig reaction between hexanal and an ylide derived from D5-iodoethane and ending with enantiomeric resolution by chiral HPLC to confirm the biochemical conversion.
(S)-2-Acetoxy-5-Undecanone, Female Sex Pheromone of the Raspberry Cane Midge, Resseliella theobaldi (Barnes)
TLDR
2-Acetoxy-5-undecanone belongs to a new group of pheromone structures in the Cecidomyiidae, most others being mono- or diesters, and is proposed to be the major component of the raspberry cane midge.
Chiral HPLC resolution of monoepoxides derived from 6,9-dienes and its application to stereochemistry assignment of fruit-piercing noctuid pheromone.
TLDR
Investigation of insect pheromonal cis-monoepoxy racemates derived from (Z,Z)-6,9-dienes revealed that an abdominal tip extract of the fruit-piercing moth, Oraesia excavata Butler, included (9S,10R)-(Z)-9, 10-epoxy-6-henicosene as a main sex pheromone component.
Optical isomers of 3,13-dimethylheptadecane: Sex pheromone components of the western false hemlock looper,Nepytia freemani (Lepidoptera: Geometridae)
TLDR
Substitutionality of pheromone stereoisomers without loss of behavioural activity has not previously been reported, but favorably compares with the concept of phersomone redundancy that was first suggested for the multiple peromone component blend of the cabbage looper moth, Trichoplusia ni.
Chirality of synergistic sex pheromone components of the western hemlock looperLambdina fiscellaria lugubrosa (HULST) (Lepidoptera: Geometridae)
TLDR
It is concluded that (7S)-7-methylheptadecane and (5S)-2,5-dimethylheptadescane are the synergistic sex pheromone components of WHL.
Chirality of 5,11-dimethylheptadecane, the major sex pheromone component of the hemlock looper,Lambdina fiscellaria (Lepidoptera: Geometridae)
TLDR
It is concluded that male antennae lack chemoreceptors for the other three stereoisomers of 5,11-dimethylheptadecane and hypothesize that only (5R,115)-5, 11-dimethyltestosterone-based pheromone is produced by female EHLs and WHLs.
...
...