Bachi M D, Korshin E E, Ploypradith P, Cumming J N, Xie S, Shapiro T A, Posner G H
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel.
Bioorg Med Chem Lett. 1998 Apr 21;8(8):903-8. doi: 10.1016/s0960-894x(98)00141-3.
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).
