Abstract
A concise and efficient synthesis of the C 13 tricyclic core of the dihydro-β-agarofuran skeleton common to the natural Celastraceae sesquiterpenoids is described. The strategy entails a Mukaiyama aldol reaction of a tetrahydronaphthalene enol silane with acetone, epoxidation, ketone reduction, and acid-catalyzed cyclization. This key scaffold was converted into diverse polyhydroxylated derivatives, which were tested for insecticidal activity.
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