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Thiol-Oxygen Cooxidation of Monoterpenes. Synthesis of Endoperoxides Structurally Related to Antimalarial Yingzhaosu A
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1998
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Antimalarial Yingzhaosu AOrganic Chemistry6-Membered Ring EndoperoxidesChemistryEndoperoxides Structurally RelatedRedox BiologyOxidative StressPhytochemicalThiol-oxygen CooxidationIntermediate Hydroperoxide-endoperoxidesBiochemistryPharmacologyNatural Product SynthesisHeterocyclicAlkene MetathesisNatural SciencesPhytochemistryMedicineDeoxygenation
The first application of thiol-oxygen cooxidation of 1,5-dienes for the preparation of 6-membered ring endoperoxides is described. Treatment of S-(-)-limonene and related monoterpenes with PhSH, dioxygen and a radical initiator, followed by selective reduction of intermediate hydroperoxide-endoperoxides afforded 4,8-dimethyl-4-phenylthiomethyl-2,3-dioxabicyclo[3.3.1]nonan-8-ols.