- Fe-catalyzed synthesis of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella)
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Starting with industrially available 1,3-dichloropropene a stereoselective process was developed for the preparation of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella) using in the key stage the Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with octylmagnesium bromide.
- Shakhmaev,Sunagatullina,Zorin
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p. 669 - 671
(2013/07/19)
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- ALKYLATION OF ACETYLCYCLOPROPANE CYCLOHEXYLIMINE BY ETHYLENE OXIDE DERIVATIVES AS A KEY STEP IN THE SYNTHESIS OF SOME INSECT ACETOGENIN PHEROMONES
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The interaction of Li derivatives of acetylcyclopropane cyclohexylimine with ethylene, propylene, and isoprene oxides leads efficiently to the corresponding γ-cyclopropylketols.The cyclopropylcarbinol corresponding to the first of them is smoothly converted under the action of the couple Me3SiBr/ZnBr2 to a linear E-C7-homoallyl bromide, which is then used in the stereocontrolled synthesis of tridec-4E-enyl and trideca-4E,7Z-dienyl acetates - components of the sex pheromones of some Lepidoptera species.Keywords: acetylcyclopropane, insect acetogenin pheromones, homoallyl rearrangement, Julia olefination, olefin oxides.
- Ivanova, N. M.,Cheskis, B. E.,Moiseenkov, A. M.,Nefedov, O. M.
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p. 1853 - 1857
(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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- LOW-MOLECULAR-MASS BIOREGULATORS. III. SYNTHESIS OF TRIDEC-4E-ENYL ACETATE-THE SEX PHEROMONE OF Keiferia lycopersicella
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A new method has been developed for the synthesis of tridec-4E-enyl acetate - the sex pheromone of the tomato pinworm Keiferia lycopersicella.
- Melikyan, G. G.,Aslanyan, G. Kh.,Atanesyan, K. A.,Mkrtchyan, D. A.,Badanyan, Sh. O.
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