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Synthesis and in vitro antimalarial activity of sulfone endoperoxides
M D Bachi1, E E Korshin, P Ploypradith
1Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel.
Bioorganic & Medicinal Chemistry Letters
|January 1, 1999
Abstract:
A series of 4,8-dimethyl-4-phenylsulfonylmethyl-2,3-dioxabicyclo[3.3.1]+ ++nonanes, carrying a variety of substituents at position-8 (4) were prepared by a short and efficient method from R-(+)-limonene. Key reactions include thiol oxygen cooxidation, and alkylation and acylation of a sterically hindered tertiary alcohol compatible with the endoperoxy functionality. Some of compounds 4, which are structurally related to yingzhaosu A (2), were found to exhibit in vitro antimalarial activity comparable to that of artemisinin (1) and superior to that of arteflene (3).