Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide
Seiya Katahara, Yasukazu Sugiyama, Mina Yamane, Yukinori Komiya, Takaaki Sato, Noritaka Chida
Abstract
A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.
Topics & Concepts
ChemistryAzomethine ylideAspidospermaLactamTotal synthesisCycloadditionKetoneCombinatorial chemistryYlideCatalysisStereochemistryOrganic chemistry1,3-Dipolar cycloadditionIndole testAdvanced Synthetic Organic ChemistryChemical synthesis and alkaloidsSynthetic Organic Chemistry Methods