Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Aza Dienes. Studies on the Total Synthesis of Lavendamycin: Investigative Studies on the Preparation of the CDE β-Carboline Ring System and AB Quinoline-5,8-quinone Ring System

Article abstract of DOI:10.1021/jo00350a069

The investigation and utilization of the inverse electron demand <4 + 2> cycloaddition of 3,5,6-tris(ethoxycarbonyl)-1,2,4-triazine with electron-rich olefins and the subsequent implementation of a palladium(0)-mediated β-carboline synthesis for the preparation of the CDE ring system of lavendamycin are detailed.Studies on the introduction and preparation of the 7-aminoquinoline-5,8-quinone AB ring system of lavendamycin are described.