Thiol-Oxygen Cooxidation of Monoterpenes. Synthesis of Endoperoxides Structurally Related to Antimalarial Yingzhaosu A

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Abstract
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.

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