Concise asymmetric total synthesis of bruceolline J

Abstract

We have developed a concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J, and a racemic approach employing an intramolecular rhodium carbenoid C–H insertion and highly regioselective gem-dimethylation reactions as key steps to synthesize bruceolline D, E along with (±)-bruceolline J.