The total synthesis of rupestines B and C, two guaipyridine sesquiterpene alkaloids, is reported. These compounds are isolated from Artemisia rupestris L. and have structural similarities to that of cananodine, a guaipyridine alkaloid with activity against two liver cancer cell lines. The synthesis of rupestines B and C was accomplished in six steps using an intramolecular Mizoroki-Heck cyclization as the key-step to form the seven-membered carbocycle of the targets. © 2020 Elsevier Ltd