Explorations on the total synthesis of (±)-isoschizogamine using an intramolecular 1,4-dipolar cycloaddition strategy

Abstract

A new strategy for the synthesis of the isoschizozygane alkaloid core has been developed that is based on a 1,4-dipolar cycloaddition reaction of a cross-conjugated heteroaromatic betaine. The required substituted piperidin-2-one needed for the eventual 1,4-dipolar cycloaddition step was prepared using an aza-Claisen rearrangement.