Synthesis of fused pyrrolines by the intramolecular cycloaddition of azides. Application to the pyrrolizidine alkaloids

Article abstract of DOI:10.1016/S0040-4039(00)89182-0

Intramolecular 1,3-dipolar cycloaddition of an azide proceeds through triazoline and vinyl aziridine, resulting in the formation of a 1,5-homodienyl shift product and two tetrahydropyrrolizines, one of which represents a formal total synthesis of supinidine.