Abstract
Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo- 9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair–boat arrangement. Subsequent treatment of endoperoxides 9 with Ag 2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro.
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