New strategy toward the diverted synthesis of oxidized abietane diterpenes via oxidation of 6,7-dehydroferruginol methyl ether with dimethyldioxirane

Abstract

A series of oxidized abietane diterpenes have been synthesized from 8,11,13-abietanotriene. The reaction of 6,7-dehydroferruginol methyl ether with dimethyldioxirane (DMDO) was carried out under various conditions. In all cases, the oxidation of positions C-6 and C-7 were observed with high selectivity when DMDO was used. When some reaction conditions, such as temperature and time were increased, 6α-hydroxysugiol was obtained. Also an interesting formation of the cis aminol derivatives was synthesized from cis epoxide 12.