31333-13-8Relevant academic research and scientific papers
Syntheses, characterizations, and biological activities of tetradeca-4,8-dien-1-yl acetates as sex attractants of leaf-mining moth of the genus Phyllonorycter (Lepidoptera: Gracillariidae)
Liblikas, Ilme,Mozuraitis, Raimondas,Santangelo, Ellen M.,Noreika, Remigijus,Borg-Karlson, Anna-Karin
experimental part, p. 1388 - 1403 (2010/04/23)
The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca-4,8-dien-1-ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB-1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB-WAX column. The isomers of tetradeca-4,8-dien-1-yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB-1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB-WAX columns. Field-screening tests for attractiveness of tetradeca-4,8-dien-1-yl acetates revealed that (4Z,8E)-tetradeca-4,8-dien-1-yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)-Tetradeca-4,8-dien-1-yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)-tetradeca-4,8-dien-1-yl acetate was attractive to Ph. cerasicolella males.
Soybean lipoxygenase and horseradish peroxidase catalysed asymmetric oxidation-reduction sequence for the synthesis of chiral (Z,E) diene-diols
Yadav,Nanda,Bhaskar Rao
, p. 787 - 788 (2007/10/03)
Unnatural synthetic substrates with a properly spaced prosthetic modifier having non-ionic hydroxy terminus undergoes soybean lipoxygenase catalysed asymmetric peroxidation followed by horseradish peroxidase induced reduction affords (Z, E)-dienediol in high enantiomeric excess.
Enzymatic asymmetric hydroxylation of unnatural substrates with soybean lipoxygenase
Yadav,Nanda,Rao
, p. 2129 - 2135 (2007/10/03)
Surrogate substrates mimicking the natural substrate (linoleic acid) bearing a spacing prosthetic group with a non-ionic hydroxyl terminus undergo asymmetric hydroxylation with soybean lipoxygenase. The prosthetic modifier supplies the missing structural features needed for enzymatic recognition and controls the regiochemical outcome of the reaction by its high hydrophobic content. The effect of pH on the regiochemistry clearly shows that all the substrates can arrange themselves at the active site of soybean lipoxygenase in only one orientation leading to formation of hydroperoxides by oxygenation at the ω-6 carbon.
Synergistic sex pheromone components of white-spotted tussock moth, Orgyia thyellina
Gries, Gerhard,Clearwater, John,Gries, Regine,Khaskin, Grigori,King, Skip,Schaefer, Paul
, p. 1091 - 1104 (2007/10/03)
In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9- one, the latter termed here 'thyellinone.' In field experiments in Japan, Z6- 11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 μg of Z6-11-one and 100 μg of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.
A Stereospecific Access to Allylic Systems Using Rhodium(II)-Vinyl Carbenoid Insertion into Si-H, O-H, and N-H Bonds
Bulugahapitiya, Priyadarshanie,Landais, Yannick,Parra-Rapado, Liliana,Planchenault, Denis,Weber, Valery
, p. 1630 - 1641 (2007/10/03)
Rhodium-catalyzed decomposition of α-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding α-silyl, α-hydroxy, α-alkoxy, α-amino, and α-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral α-vinyldiazoesters and Doyle's chiral catalyst Rh2(MEPY)4. In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh2(MEPY)4-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.
(Carboxyalkyl)benzyl propargyl ethers as selective inhibitors of leukocyte-type 12-lipoxygenases
Gorins, Gilles,Kuhnert, Lethea,Johnson, Carl R.,Marnett, Lawrence J.
, p. 4871 - 4878 (2007/10/03)
A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2- tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 μM) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.
Rhodium(II)-vinylcarbenoid insertion into the Si - H bond. A new stereospecific synthesis of allylsilanes
Landais, Yannick,Planchenault, Denis,Weber, Valery
, p. 9549 - 9552 (2007/10/02)
Rh2(OAc)4 catalysed decomposition of vinyldiazocarbonyl compounds in the presence of organosilanes led stereospecifically to the corresponding allylsilanes in good yields. An asymmetric approach has also been considered as well as the extension of the methodology to the synthesis of other allylic systems.
Chlorocodlemones
Tellier, F.,Hammoud, A.,Ratovelomanana, V.,Linstrumelle, G.,Descoins, C.
, p. 281 - 286 (2007/10/02)
Chlorinated analogs of codlemone have been prepared by palladium-catalyzed reactions of functionalized organometallics with (E) and (Z) 1,2-dichloroethylenes.Key words: pheromone analogs / conjugated chlorodienes / stereoselective synthesis
A Stereoselective Synthesis of Trisubstituted Alkenes. Part 1. Nickel-catalysed Coupling of Grignard Reagents with 5-Alkyl-2,3-dihydrofurans
Kocienski, Philip J.,Pritchard, Martin,Wadman, Sjoerd N.,Whitby, Richard J.,Yeates, Clive L.
, p. 3419 - 3430 (2007/10/02)
5-Alkyl-2,3-dihydrofurans 3a-j prepared by the alkylation of 5-lithio-2,3-dihydrofuran 2 with primary alkyl bromides and iodides, undergo Ni(0)-catalysed coupling with Grignard reagents to give homoallylic alcohols.The yield and stereoselectivity depend on the structure of the Grignard reagent with the best results being obtained with long chain primary Grignard reagents and Grignard reagents lacking β-hydrogens (Me, Ph, Me3SiCH2). 5-(1-Hydroxyalkyl)-2,3-dihydrofurans 20 and 21 are poor substrates for the coupling reaction.Mechanisms are proposed for the coupling as well as competing reduction and isomerisation reactions.
COMPOUNDS WITH GREEN PLANT FRAGRANCE. IV. SUBSTITUTED CIS-3-ALKEN-1-OLS
Vasil'ev, A. A.,Cherkaev, G. V.,Nikitina, M. A.
, p. 220 - 225 (2007/10/02)
Syntheses are reported for leaf alcohol analogs, namely, substituted cis-3-alken-1-ols.Many of these compounds have green plant fragrance similar to that of a leaf alcohol standard (cis-3-hexen-1-ol).
