Abstract
Synthesis of β-sulfenyl endoperoxides 9 was achieved by a four component sequential free radical reaction based on the application of the thiol-olefin-co-oxygenation reaction to monoterpenes, followed by in situ treatment with triphenylphosphine. β-Sulfenyl endoperoxides 9 were oxidized with m-CPBA to β-sulfonyl endoperoxides 10. This process provides an efficient method for the preparation of peroxides containing the 2,3-dioxabicyclo[3.3.1]nonane system (2) characteristic of antimalarial agents of the yingzhaosu A (3) family. A simple NMR diagnostic tool for the identification of stereoisomers is described.
Original language | English |
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Pages (from-to) | 2449-2469 |
Number of pages | 21 |
Journal | Tetrahedron |
Volume | 58 |
Issue number | 12 |
DOIs | |
State | Published - 18 Mar 2002 |
Externally published | Yes |
Keywords
- Antimalarial peroxides
- Free radicals
- Multi-component reaction
- Sequential reactions
- Thiol olefin co-oxygenation reaction