17643-36-6Relevant articles and documents
Improved synthesis of (Z,E)-9,11,13-tetradecatrienal, the sex pheromone of the Carob Moth Apomyelois (=Ectomyelois) ceratoniae (Lepidoptera: Pyralidae)
Noorbakhsh, Saeede,Alizadeh, Babak Heidary,Saber, Moosa,Farazmand, Hossein
, p. 199 - 201 (2017)
(Z,E)-9,11,13-Tetradecatrienal is a sex pheromone component emitted by virgin females of the Carob Moth Apomyelois ceratoniae Zeller (Lepidoptera: Pyralidae) which is an important pest of Iranian pomegranate fruits. Chemical control of this pest is not possible and biological methods with pheromones are used. The synthesis of the major component of the sex pheromone was achieved in fewer steps and with lower cost than previously. (Z,E)-9,11,13-Tetradecatrienal was synthesised by four steps with 59% overall yield. The coupling of a conjugated dienynol intermediate from E-1,2-dichloroethylene with vinyl magnesium bromide was achieved in good yield and followed by reduction of dienynol with activated zinc in THF-H2O and oxidation gave the aldehyde of the sex pheromone.
A large scale and concise synthesis of γ-linolenic acid from 4- chlorobut-2-yn-1-ol
Durand, Sandrine,Parrain, Jean-Luc,Santelli, Maurice
, p. 1015 - 1018 (1998)
A large scale and concise synthesis of γ-linolenic acid is described. The key step of the synthesis involves a copper salt mediated cross-coupling of two different alkynes and chlorobutynol.
Structure based interference with insect behaviour - Cyclopropene analogues of pheromones containing Z-alkenes
Al Dulayymi, Juma'a R.,Baird, Mark S.,Simpson, Michael J.,Nyman, Susan,Port, Gordon R.
, p. 12509 - 12520 (1996)
Analogues of the pheromones of three insect species (Musca domestica L., Plutella xylostella L. and Ephestia elutella Hbn.) in which a Z-alkene has been replaced by a 1,2-disubstituted cyclopropene have been synthesized. The analogues interfere with normal mating behaviour for each species.
The first stereoselective synthesis of a dithiane derivative of the C18 β-diketodiene system proposed for an active compound isolated from Cantharellus cibarius (chanterelle)
Grodner, Jacek,Golebiewski, W. Marek,Willis, Michael C.,Osborne, James D.,Gucma, Miros?aw
, p. 1181 - 1189 (2015)
A stereocontrolled synthesis of a thioketal system that is a direct precursor of an active compound isolated from chanterelle was accomplished by using readily available methyl 11-[2-(2-oxoethyl)-1,3-dithian-2-yl]undec-9-ynoate as a key intermediate. The synthesis involves simple and straightforward reactions, such as addition of a lithiated alkyne to an aldehyde, alkyne hydrogenation using nickel boride, alcohol oxidation with Dess-Martin periodinane, and Z-to-E enone isomerization.
Synthesis of dansyl-labeled probe of thiophene analogue of annonaceous acetogenins for visualization of cell distribution and growth inhibitory activity toward human cancer cell lines
Kojima, Naoto,Suga, Yuki,Matsumoto, Takuya,Tanaka, Tetsuaki,Akatsuka, Akinobu,Yamori, Takao,Dan, Shingo,Iwasaki, Hiroki,Yamashita, Masayuki
, p. 1276 - 1283 (2015)
The convergent synthesis of the dansyl-labeled probe of the thiophene-3-carboxamide analogue of annonaceous acetogenins, which shows potent antitumor activity, was accomplished by two asymmetric alkynylations of the 2,5-diformyl THF equivalent with an alkyne having a thiophene moiety and another alkyne tagged with a dansyl group. The growth inhibitory profiles toward 39 human cancer cell lines revealed that the probe retained the biological function of its mother compound, and would be useful for studying cellular activity.
Synthesis of the (17R)- and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretion of the beet armyworm
Itoh, Seiji,Kuwahara, Shigefumi,Hasegawa, Morifumi,Kodama, Osamu
, p. 1591 - 1596 (2002)
Both the (17R)- and (17S)-isomers of volicitin, which is contained in the oral secretion of the beet armyworm and induces corn seedlings to emit a blend of volatile compounds to attract the natural enemy of the herbivore, were synthesized via the semi-hyd
The synthesis and biological evaluation of a kabiramide C fragment modified with a WH2 consensus actin-binding motif as a potential disruptor of the actin cytoskeleton
Tetlow, Daniel J.,Winder, Steve J.,A?ssa, Christophe
, p. 807 - 810 (2016)
The F-actin depolymerisation potency of a fragment of kabiramide C was increased when modified with a WH2 consensus actin-binding motif LKKV. Despite its low affinity for actin monomers, a shorter analogous fragment not bearing LKKV was identified as a potent inhibitor of actin polymerisation and a promoter of its depolymerisation, resulting in a loss of actin stress fibres in cells.
Partially fluorinated analogs of (Z)-9-dodecenyl acetate: Probes for pheromone hydrophobiclty requirements
Sun, Wei-Chuan,Prestwich, Glenn D.
, p. 801 - 804 (1990)
Allylic difluoromethylene, terminal trifluoromethyl, and pentafluoroethyl analogs of (Z)-9-dodecenyl acetate were synthesized to probe the requirements for hydrophobicity of the alkyl terminus in pheromone activity. These compounds show unexpected and varied behavioral activities in assays using the European grape berry moth.
Tetris in monolayers: Patterned self-assembly using side chain shape
Xue, Yi,Zimmt, Matthew B.
, p. 8832 - 8834 (2011)
The "kinked" shapes of conjugated alkadiynes constrain chain packing in monolayers on HOPG. Centrally located diyne units permit assembly of 1,5-bis(alkadiyne)anthracene monolayers. Off-center diynes inhibit self-assembly. Shape matched pairs of off-center diyne chains direct self-assembly of compositionally patterned, two component monolayers.
Stereodirectional synthesis of the main component of pheromone (9Z,12E)-tetradeca-9,12-dienyl acetate by cross-coupling
Matveeva,Erin,Leshcheva,Kurts
, p. 765 - 770 (2000)
By cross-coupling of alkynyl cuprate with crotyl halides was synthesized (9Z,12E)-tetradeca-9-12-dienyl acetate, the main component of pheromones of several insect species Lepidoptera. The assignment of the chemical shifts of diene system was performed by 1H and 13NMR spectroscopy.
