A unified synthesis of topologically diverse Aspidosperma alkaloids through divergent iminium-trapping

Abstract

Five Aspidosperma alkaloids within three structurally diverse topologies were synthesized from a single key intermediate, which could be selectively driven through three reaction paths: N(1)- vs. C(3)-indole cyclization vs. over-reduction, via the incorporation of conformational and electronic constraints that influence the reactivity of its derived iminium ion 7.