Synthesis of amorpha-4,11-diene from dihydroartemisinic acid

Geoffrey Schwertz (1, 2) , Andrea Zanetti (1, 2) , Marllon Nascimento de Oliveira (1, 2) , Mario Andrés Gómez Fernández (1, 2) , Fabienne Dioury (2) , Janine Cossy (1) , Zacharias Amara (2)

1 CBI - Chimie-Biologie-Innovation (UMR 8231)
2 GBCM - Laboratoire Génomique, bioinformatique et chimie moléculaire

Amorphadiene is a natural product involved in the biosynthesis of the antimalarial drug artemisinin. A convenient four-step synthesis of amorphadiene, starting from commercially available dihy-droartemisinic acid, is reported. The targeted molecule is isolated with an overall yield of 85% on a multi-gram scale in four steps with only one chromatography.

Domains: Organic chemistry; Medicinal Chemistry

Geoffrey Schwertz, Andrea Zanetti, Marllon Nascimento de Oliveira, Mario Andrés Gómez Fernández, Fabienne Dioury, et al.. Synthesis of amorpha-4,11-diene from dihydroartemisinic acid. Tetrahedron, 2019, 75 (6), pp.743-748. ⟨10.1016/j.tet.2018.12.050⟩. ⟨hal-02502402⟩