Rapid Synthesis of Ismine, a Bioactive Amaryllidaceae Alkaloid

Ismine (6-[2-(methylamino)phenyl]-1,3-benzodioxole-5-methanol, 1), a biologically active alkaloid, has been synthesised by a rapid and simple four-step sequence. This synthesis involved a consecutive aryl–aryl and N–aryl coupling, leading to a phenanthridine derivative in a one-pot sequence, which employed a palladium catalyst and trifurylphosphine as the ligand. This synthesis gave an overall yield of 23%.