- Method for preparation of Octadecadienyl acetate as major sex pheromone of cherry tree borer, Synanthedon bicingulate
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The present invention relates to a method for producing a sex pheromone of cherry tree borer (Synanthedon bicingulata) in an attempt to control the same. More specifically, provided is a method for stereoselectively producing high purity (3E,13Z)- octadecadienyl acetate and (3Z,13Z)-octadecadienyl acetate respectively which are major sex pheromones of cherry tree borer from a cheap starting material in an efficient, simple, and economically feasible way.COPYRIGHT KIPO 2018
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Paragraph 0079; 0084-0086
(2018/06/26)
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- Sequential alkynylation of ω-bromoalkyl triflates: Facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones
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Sequential treatment of ω-bromoalkyl triflates with an alkynyllithium at 0°C followed by addition of a second alkynyllithium and NaI and heating the reaction mixture provides a simple one-pot access to unsymmetrical diynes in good yields. These diynes may be transformed stereoselectively into diene pheromones such as (Z,Z)- and (E,Z)-3,13-octadecadienyl acetate. Graphical Abstract
- Armstrong-Chong, Rosemary J.,Matthews, Kristopher,Chong, J. Michael
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p. 10239 - 10244
(2007/10/03)
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- A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones
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(equation presented) A new, convergent synthesis of (E,Z)-2,13-octadecadienyl acetate (1) and (E,Z)-3,13-octadecadienyl acetate (2), the two key components of the leopard moth Zeuzera pyrina, from 2-chloromethyltetrahydrofuran in good overall yields and stereomeric purity is reported. The synthesis of both components utilizes the common intermediate sulfone 12 as a convenient building block to be coupled with iodoacetylenic derivatives 9 or 17 in the key step.
- Capdevila, Anna,Prasad, Attaluri R.,Quero, Carmen,Petschen, Ine?s,Bosch, Maria P.,Guerrero, Angel
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p. 845 - 848
(2008/02/09)
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- SYNTHESIS OF TRANS-2,CIS-13- AND TRANS-3,CIS-13-OCTADECADIEN-1-OL ACETATES, COMPONENTS OF THE SEX PHEROMONE OF SYNANTHEDON TIPULIFORMIS (LEPIDOPTERA, SISIIDAE)
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The Wittig-Horner reaction of ethoxycarbonylmethylenetriphenylphosphorane or ethyl diethylphosphonoacetic acid with cis-11-hexadecenal and the modified Knoevenagel reaction of this aldehyde with malonic acid gave the ethyl ester of trans-2,cis-13-octadecadienoic acid and trans,cis-13-octadecadienoic acid, which upon reduction and acetylation were converted into trans-2,cis-13- and trans-3-cis-13-octadecadien-1-yl acetates, which are components of the sex pheromone of Synanthedon tipuliformis (Lepidoptera, Sisiidae).
- Sorochinskaya, A.M.,Kovalev, B.G.
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p. 621 - 624
(2007/10/02)
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- Stereoselective synthesis of (Z,Z)-3, 13-octadecadien-1-ol, (Z,Z)-3, 13-octadecadien-1-yl acetate and their (E,Z)isomers
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(Z,Z)-3,13-Octadecadien-1-ol (VIII), (Z,Z)-3,13-octadecadien-1-yl acetate (IX) and their corresponding (E,Z) isomers (X and XI) have been synthesized via Li2CuCl4 catalysed coupling reaction of (Z)-8-tridecylmagnesium bromide with mesylate (II) as a key step.
- Trehan, I R,Kad, G L,Singh, Vasundhara,Vig, Rakesh
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p. 563 - 566
(2007/10/02)
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- EFFICIENT SYNTHESIS OF 3E,13Z-OCTADECADIENOL, ITS ACETATE, 4E,6E,11Z-HECADECATRIENAL, AND 4E,6E,11Z-HEXADECATRIENYL ACETATE, SEX PHEROMONES OF SOME LEPIDOPTERAN SPECIES
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The title linear acetogenins have been synthesized by a strategy of joining acetylcyclopropane to 8Z-tridecenol or 5Z-decenol prepared after Julia, leading to the corresponding secondary cyclopropylcarbinols.The ZnBr2/Me3SiBr-initiated homoallylic rearrangement of the latter assures at a key step the stereospecific construction of transoid fragments of the target molecules.
- Ivanova, N. M.,Cheskis, B. A.,Moiseenkov, A. M.,Nefedov, O. M.
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p. 2196 - 2204
(2007/10/02)
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- Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones
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Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.
- Moiseenkov, Alexander M.,Czeskis, Boris A.,Ivanova, Natalya M.,Nefedov, Oleg M.
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p. 2639 - 2649
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 2,13- AND 3,13-OCTADECADIENYL ACETATES, SEX PHEROMONE COMPONENTS OF THE Synanthedon SPECIES
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The sex pheromone components of several Synanthedon species, 2,13- and 3,13- octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation.Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30percent overall yields.Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene.The title pheromones were generated in more than 97percent stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.
- Hoskovec, Michal,Saman, David,Koutek, Bohumir
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p. 2270 - 2281
(2007/10/02)
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- SYNTHESIS OF PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION
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The reactions of nonstabilized triphenylphosphorus ylides with aldehydes have been studied in detail.The stereochemistry and yields of the alkene products are highly dependent upon base used for the generation of the ylide, the solvent and reaction temperature.The synthesis of sex pheromone components by Wittig reaction are also described.
- Vinczer, Peter,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba
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p. 797 - 820
(2007/10/02)
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- SIMPLE AND STEREOCONTROLLED SYNTHESIS OF AN OPTIMAL ISOMERIC MIXTURE OF 3,13-OCTADECADIEN-1-YL ACETATES
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A simple route has been developed for the preparation of the optimal isomeric mixture of 3,13-octadecadien-1-yl acetates (ODDA) which is the active sex pheromone of many Synanthedon species.The stereocontrolled formation of double bonds have been achieved via Wittig reaction and subsequent reduction of C-C triple bond.
- Vinczer, Peter,Baan, Gabor,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba
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p. 1257 - 1270
(2007/10/02)
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- Preparation of unsaturated aliphatic insect pheromones using cyclic phosphonium ylids
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This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.
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