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Synlett 1998; 1998(2): 122-124
DOI: 10.1055/s-1998-1587
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Thiol-Oxygen Cooxidation of Monoterpenes. Synthesis of Endoperoxides Structurally Related to Antimalarial Yingzhaosu A

Mario D. Bachi* , Edward E. Korshin
  • *Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot 76100, Israel; Fax +9 72-8-9 34 41 42; E-mail: cobachi@weizmann.weizmann.ac.il
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Publikationsdatum:
31. Dezember 2000 (online)

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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.

2,3-dioxabicyclo[3.3.1]nonane - cyclic peroxide - sequential reaction - peroxy radicals - thiyl radicals