Rapid entry to phenanthroindolizidine alkaloids via an acid-catalysed acyliminium ion-electrocyclization cascade†
Max St. Pierre,Christine J. Kempthorne,David K. Liscombe,James McNulty
Organic & Biomolecular Chemistry Pub Date : 08/29/2023 00:00:00 , DOI:10.1039/D3OB01359F
Abstract

A rapid total synthesis of seco-phenanthroindolizidine alkaloids was achieved involving a one-pot acid catalyzed deprotection- condensation-electrocyclization strategy. This synthetic route provided a concise synthesis of (±)-seco-antofine and (±)-septicine in only 4 steps with an overall yield of 22% and 17%, respectively.

Graphical abstract: Rapid entry to phenanthroindolizidine alkaloids via an acid-catalysed acyliminium ion-electrocyclization cascade