Synthesis of disubstituted 1,2-dioxolanes, 1,2-dioxanes, and 1,2-dioxepanes |
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| Authors: | Francisco M. Guerra,Marí a J. Ortega,F. Javier Moreno-Dorado |
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| Affiliation: | a Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Polígono Río San Pedro s/n, 11510 Puerto Real, Cádiz, Spain
b Departamento de Química Orgánica, Facultad de Ciencias, Polígono Río San Pedro s/n, 11510 Puerto Real, Cádiz, Spain |
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| Abstract: | A route to cyclic peroxides containing 1,2-dioxolane, 1,2-dioxane or 1,2-dioxepane rings is described. These compounds present simpler structures related to the bicyclic core of stolonoxides, metabolites with marked cytotoxicity against several mammalian tumor cell lines, isolated from the marine tunicate Stolonica socialis. The key synthetic step consists in the intramolecular Michael addition of a secondary hydroperoxide group to an α,β-unsaturated ester. |
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| Keywords: | Cyclic peroxides Hydroperoxide cyclization Bioactivity Stolonoxides |
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