Biological Activity of the Chiral Sex Pheromone of the Peach Leafminer Moth, Lyonetia clerkella LINNE(Lepidoptera : Lyonetiidae)

Sato, Rikio; Abe, N.; Sugie, Hajime; Kato, Minoru; Mori, Kenji; Tamaki, Yoshio

doi:10.1303/aez.21.478

Cited by 14 publications

(5 citation statements)

References 2 publications

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“…As an example to demonstrate the potential of the methodology described herein, we decided to synthesize ( S )-14-methyloctadec-1-ene (Scheme ), the female sex pheromone of the peach leafminer moth ( Lyonetia clerkella ). Infestation by this insect causes almost complete defoliation of the trees and reduces cropping and fruit production potential for the future, which typically affects to fruit trees such as apple, pear, cherry, plum, quince, and peach . The synthesis of this compound was easily accomplished starting from amide 2a , which was prepared previously by us by asymmetric conjugate addition of n -BuLi to ( S,S )-(+)-pseudoephedrine crotonamide 1a .…”

Section: Results and Discusionmentioning

confidence: 99%

(S,S)-(+)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation Reactions

et al. 2006

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Organolithium reagents undergo highly regio- and diastereoselective 1,4-addition to (S,S)-(+)-pseudoephedrine enamides furnishing the corresponding beta-alkyl-substituted adducts in excellent yields and diastereoselectivities. In addition, the intermediate lithium enolates generated after the conjugate addition step undergo a highly diastereoselective alkylation reaction, furnishing alpha,beta-dialkyl-substituted amides in high yields. The obtained adducts have been converted into chiral nonracemic beta-alkyl- and alpha,beta-dialkyl-substituted carboxylic acids and gamma-alkyl- and beta,gamma-dialkyl-substituted alcohols using very simple and high-yielding procedures.

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Section: Results and Discusionmentioning

confidence: 99%

(S,S)-(+)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation Reactions

et al. 2006

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“…This study is the first successful application of chiral HPLC to methyl-branched pheromones, and it is noteworthy that enantiomers of less polar volatiles showed different chromatographic behaviors on a chiral HPLC column. Several sex pheromones with a chiral center at a methyl-branched position have been identified from lepidopteran species, and their stereochemistry has been reported as follows: (R)-10-methyldodecyl acetate in Adoxophyes honma (Tamaki et al 1983), (S)-14-methyl-1-octadecene in Leucoptera clerkella (Sato et al 1986), (5S,9S)-5,9-dimethylheptadecane in L. scitella (Tóth et al 1989), (5R,11S)-5,11-dimethylheptadecane in Lambdina fiscellaria fiscellaria (Li et al 1993a), (S)-2,5-dimethylheptadecane in Lambdina fiscellaria lugubrosa (Li et al 1993b), (S)-7-methylheptadecane and meso-7,11-dimethylheptadecane in L. athasaria and L. pellucidaria (Duff et al 2001), and (3S,13R)-3,13-dimethylheptadecane in Nepytia freemani (King et al 1995). All of the absolute configurations were presumed by bioassays with synthetic stereoisomers, but direct instrumental analyses have never been accomplished.…”

Section: Discussionmentioning

confidence: 99%

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

et al. 2010

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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 positional isomers with a methyl branch at the 4-, 5-, 7-, 13-, or 15-position (4-8, respectively) were synthesized. The GC-MS analyses revealed that natural components I and II were best fitted with those of 1 and 2, respectively, among the methyl-2-octadecanones examined, indicating the usefulness of this analytical instrument and authentic standards for the determination of the positions of methyl branches. In field trapping tests, 4-8 could not substitute for 1 or 2, nor did these compounds inhibit the active binary lure of 1 and 2, indicating that the males strictly recognized the 2-ketones with a methyl branch at the 6- or 14-positions. Next, the absolute configurations of I and II were determined by HPLC with a normal-phased chiral column (Chiralpak AD-H), which could separate the enantiomers of both 1 and 2. The chiral HPLC analysis of a crude pheromone extract indicated that the females exclusively produced (S)-1 and (S)-2. Furthermore, a field evaluation of each enantiomer revealed that (S)-1 and (S)-2 were bioactive but (R)-1 and (R)-2 were not.

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“…Bello 等 [46] 图式 [47][48] , 是目前不对称合成研究领域的热点 [49][50] . (S)-14-甲基-1-十八碳烯(4)是桃潜叶蛾(Lyonetia clerkella)性信息素的主要活性成分 [51][52] , 具有诱捕雄蛾的作用 [53][54] . 周其林等 [55] [56][57] .…”

Section: 单手性甲基脂肪烃类昆虫信息素的合成unclassified

Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones

Yuan¹,

Bian²,

Wang³

et al. 2021

Chinese Journal of Organic Chemistry

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The chiral methyl-branched aliphatic hydrocarbon insect pheromones including single, double and multichiral methyl-branched insect pheromones are the most promising green control of Scoliopteryx libatrix, Monochamus titillator, Lyonetia clerkella and other many pests. The syntheses of single chiral methyl-branched pheromones are reviewed according to the methods of constructing chiral methyl, whereas the preparation of double chiral methyl-branched and multichiral methyl-branched ones are illustrated on the basis of the linking strategies of the key fragments. Moreover, the advantages and disadvantages of the synthetic approaches are discussed, as well as the prospects for the synthesis of chiral methyl-branched aliphatic hydrocarbon insect pheromones.

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Biological Activity of the Chiral Sex Pheromone of the Peach Leafminer Moth, Lyonetia clerkella LINNE(Lepidoptera : Lyonetiidae)

Cited by 14 publications

References 2 publications

(S,S)-(+)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation Reactions

(S,S)-(+)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation Reactions

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

Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones

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