Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.) p. 1853 - 1857 (1992)
Update date:2022-08-03
Topics:
Ivanova, N. M.
Cheskis, B. E.
Moiseenkov, A. M.
Nefedov, O. M.
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.
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