A convenient route to 1-(2-oxiranyl)-1,4-diketones and their application to the synthesis of endo-brevicomin, endo-isobrevicomin, frontalin and related compounds via alkylated 6,8-dioxabicyclo[3.2.1]octan-2-ones |
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Authors: | Vladimir I Tyvorskii Dmitry A Astashko Oleg G Kulinkovich |
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Institution: | Department of Organic Chemistry, Belarusian State University, Fr. Scorina Avenue, 4, 220050 Minsk, Belarus |
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Abstract: | 1-(2-Oxiranyl)-1,4-alkanediones were prepared from the ethylene acetals of ethyl 4-oxoalkanoates via the oxidation of the intermediate 1,2-dialkylcyclopropanols having a protected carbonyl group in an aliphatic chain. Intramolecular acetalization of these epoxy dicarbonyl compounds gave alkylated 6,8-dioxabicyclo3.2.1]octan-2-ones in good yields. The latter were found suitable to be precursors for (±)-endo-brevicomin and its 2-hydroxy derivative, as well as (±)-endo-isobrevicomin and (±)-frontalin. |
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Keywords: | Cyclopropanols Oxidation Oxiranes 1 4-Dicarbonyl compounds Pheromones |
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