Convenient synthesis of perhydrobenz[e]indene triketone, a key intermediate for the total synthesis of stelletins

Abstract

A complementary strategy for the formal total synthesis of (±)-stelletins is reported. Key reactions include a diastereoselective Eschenmoser–Claisen rearrangement, a highly diastereoselective alkylation of decalin-nitrile, and an intramolecular [3 + 2] cycloaddition/N–O reductive bond cleavage to construct the strained functionalized tricyclic core of (±)-stelletins.