Expedient Syntheses of Antofine and Cryptopleurine via Intramolecular 1,3-Dipolar Cycloaddition

摘要

The practical and expedient total syntheses of the representative phenanthroindolizidine and phenan-throquinolizidine alkaloids, antofine and cryptopleurine, are described. Construction of the pyrrolidine and piperidine ring of each alkaloid was achieved by using an intramolecular 1,3-dipolar cycloaddition of an azide onto an alkene and subsequent reduction of the resulting imine and aziridine.