Aspastipulines and Portulacatone are pyrrolo-azepine containing alkaloids isolated from Asparagus stipularis forssk roots and Portulaca oleracea, respectively that have significant anticancer properties and moderate anti-inflammatory activities. Herein, we report the first total synthesis of five Pyrrolo-azepine containing aspastipuline, portulacatone and related alkaloids from a commercially available starting materials, ethyl 1H-pyrrole-2-carboxylate, via TFAA mediated intramolecular Friedel-Crafts acylation as a key step in concise route with good overall yield. © 2023 Elsevier Ltd