Abstract
Obtaining cuparene-type sesquiterpenes is a significant synthetic challenge mainly because of the construction of the sterically hindered quaternary centres. We report herein the successful construction of such quaternary moiety by a highly regioselective opening of (+/−)-2,5-dimethoxy-4-methyl-α-methylstyrene oxide by the acetone silyl enol ether catalysed by Lewis acid. Additionally, an efficient epoxidation of the highly activated 2,5-dimethoxy-4-methyl-α-styrene was accomplished by modifications on the dioxirane-promoted epoxidation protocol. Intensive optimisations for both key steps allowed the synthesis of the desired branched homo-aldol adduct, proposed as a key intermediate for a short synthetic alternative towards enokipodins.
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