Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 6,14-dimethyl-2-octadecanone, and 14-methyl-2-octadecanone, the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma

All of the stereoisomers of the components of the female-produced sex pheromone of a moth, Lyclene dharma dharma, were synthesized. They are (R)- and (S)-6-methyl-2-octadecanone, (6R,14R)-, (6R,14S)-, (6S,14R)-, and (6S,14S)-6,14-dimethyl-2-octadecanone, and (R)- and (S)-14-methyl-2-octadecanone. Enantiomers of citronellal and methyl (S)-3-hydroxy-2-methylpropanoate were the starting materials, and olefin cross metathesis was employed as the key reaction.     

Absolute configuration of gomadalactones A, B and C, the components of the contact sex pheromone of Anoplophora malasiaca

Absolute configuration of gomadalactones A (1), B (2) and C (3), the pheromone components of the white-spotted longicorn beetle (Anoplophora malasiaca) was assigned as (1S,4R,5S)-1, (1R,4R,5R)-2 and (1S,4R,5S,8S)-3 by comparing their published CD spectra with those of (1R,5R)-(+)-4,4,8-trimethyl-3-oxabicyclo[3.3.0]oct-7-ene-2,6-dione (4) and (1S,5R,8S)-(+)-4,4,8-trimethyl-3-oxabicyclo[3.3.0]octane-2,6-dione (5) prepared from (R)-(−)-carvone (6).     

Minor components with the γ-cyclogeranil geraniol skeleton from Bellardia trixago (L.) all.

Trixagol 1 and fourteen derivatives with the skeleton of γ-cyclogeranil geraniol were isolated from Bellardia trixago, the structures were determined by spectroscopic methods and confirmed by partial synthesis. Furthermore. 3,4-dihydro-γ-ionone, α-ambrinol, β-sitosterol and three flavonoids 5-O-demethyl tangeretin, 5-hydroxy auranetin and 3′-methoxy calycopterin were also isolated.     

Synthesis of (-)-periplanone-B a sex pheromone component of the American cockroach (periplaneta americana)

The naturally occurring (-)-enantiomer of periplanone-B was synthesized stereoselectively starting from (S)-3-cyclohexene-1-carboxylic acid. The crystalline pheromone was obtained in 12% overall yield through 18 steps.     

Chiral synthesis of (2s,3s,7s)-3,7-dimethylpentadecan-2-yl acetate and propionate,potential sex pheromone components of the pine saw-fly neodiprion sertifer (geoff.)

A synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate ($\text{2}$) and propionate ($\text{3}$) is described. (2S)-2-Methyldecan-1-yl lithium ($\text{5}$) was reacted with (3S,4S)-3,4-dimethyl-γ-butyrolactone ($\text{6}$) to yield the ketoalcohol $\text{19}$ which upon Huang-Minlon reduction furnished (2S,3S,7S)-3,7-dimethylpentadecan-2-ol ($\text{1}$). Acylations gave the esters $\text{2}$ and $\text{3}$. The (2S)-2-methyldecan-1-yl lithium was obtained via asymmetric synthesis. The chiral lactone $\text{6}$ was obtained from (2S,3S)-trans-2,3-epoxybutane and dimethyl malonate.     

Stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones: sex pheromone components of the painted apple moth Teia anartoides

The stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones, sex pheromone components of the painted apple moth, Teia anartoides, is reported using the Suzuki-coupling of vinyl boronic acid and vinyl iodide intermediates.     

A simple and cost effective synthesis of 3,11-dimethylnonacosan-2-one, a female sex pheromone of the German cockroach

A convenient synthesis of 3,11-dimethylnonacosan-2-one (1) is described. Our strategy involves the use of well known C-alkylation and ethyl acetoacetate synthesis reactions as key steps. We expect that this method will prove to be useful for large scale preparation of 1 and modification of dimethylnonacosanones.     

Enantiospecific synthesis of (S)-(+)-3-methylheneicosan-2-one, an analog of the sex pheromone of the German cockroach (Blatella germanica L.) from (−)-(1R,4S)-menthone

An enantiospecific synthesis of (S)-(+)-3-methylheneicosan-2-one, an analog of the sex pheromone of the German cockroach (Blatella germanica L.), was carried out through selective transformations of (3R,6S)-3,7-dimethyloctane-6-olide obtained from (−)-menthonevia the Baeyer—Villiger reaction. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1071–1073, May, 1997.     

Synthesis of all the four stereoisomers of (1′S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Paulownia bagworm, Clania variegata

All the four stereoisomers of (1′S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate, the major component of the sex pheromone of Clania variegata, were synthesized by starting from (R)- or (S)-2-methylbutan-1-ol, (R)- or (S)-citronellal, and (S)-2-methylpentan-3-ol. Olefin cross metathesis was employed as the key reaction.     

Synthesis of 6Z,8E-heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides

6Z,8E-Heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides has been prepared in seven steps from 1,2-epoxydodecane in an overall yield of 25%.     

Chemical studies on the anobiidae: Sex pheromone of the drugstore beetle, stegobium paniceum (L.) (coleoptera)

Chemical an spectroscopic evidence is presented to show that 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one (10) is the sex pheromone produced by the female drugstore beetle, Stegobium paniceum L.     

Synthesis of sidisterone, a phytoecdysteroid from Silene dioica (L.) Clairv.

The first synthesis of the natural phytoecdysteroid sidisterone is realized. It is based on the isoxazoline ring reductive cleavage of 20-hydroxy-20-isoxazolynylecdysterone, acid-catalyzed cyclization of the resultant ketodiol into a dihydrofuran derivative, and ozonolysis of the exocyclic double bond of the latter.     

Stereospecific synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor

A short and completely stereospecific synthesis of (E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate, the very recently identified sex pheromone of the passionvine mealybug Planococcus minor, is described. In the key step, CuI-catalyzed anti-addition of a Grignard reagent to a propargyllic alcohol intermediate gave the required trisubstituted alkene with 100% regio- and stereospecificity. The stereochemical purity of the pheromone is critically important because the (Z)-isomer is a powerful behavioral antagonist.     

Identification of the sex pheromone of Phyllophaga cuyabana (Coleoptera: Melolonthidae)

Phenol 1 and p-cresol 2 were identified as sex pheromone components released by females Phyllophaga cuyabana. The compounds are produced in a ratio of 1:1, as detected by the analysis of pheromone gland extract. In field experiments, the capture of males in traps baited with the synthetic blend were significantly higher than in control traps.     

(9Z)-9,13-Tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer

The highly unsaturated aldehyde (9Z)-9,13-tetradecadien-11-ynal and the corresponding alcohol were identified as possible sex pheromone components of the avocado seed moth, Stenoma catenifer. The aldehyde as a single component attracted more male moths than caged virgin female moths, and addition of the analogous alcohol and/or acetate decreased attraction. A stereospecific synthesis of the pheromone is described.     

Synthesis of the Janus integer pheromone (4R,9Z)-9-octadecen-4-olide

The synthesis of (4R,9Z)-9-octadecen-4-olide 1, the female sex pheromone of Janus integer is reported using a Zipper isomerization reaction as the key step.