Journal
TETRAHEDRON
Volume 66, Issue 1, Pages 157-163Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.026
Keywords
Cyclic peroxides; Hydroperoxide cyclization; Bioactivity; Stolonoxides
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Funding
- Ministerio de Educacion y Ciencia (Spain)
- FEDER [CTQ200402361]
- Junta de Andalucia [FQM-285, FQM-169]
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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 alpha,beta-unsaturated ester. (C) 2009 Elsevier Ltd. All rights reserved.
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