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

Geoffrey Schwertz; Andrea Zanetti; Marllon Nascimento de Oliveira; Mario Andrès Gomez Fernandez; Fabienne Dioury; Janine Cossy; Zacharias Amara

doi:10.1016/j.tet.2018.12.050

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

Tetrahedron. 2019 Feb 8;75(6):743-748. doi: 10.1016/j.tet.2018.12.050.

Authors

Geoffrey Schwertz^{1

2}, Andrea Zanetti^{1

2}, Marllon Nascimento de Oliveira^{1

2}, Mario Andrès Gomez Fernandez^{1

2}, Fabienne Dioury², Janine Cossy¹, Zacharias Amara²

Affiliations

¹ Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231, ESPCI ParisTech/CNRS/PSL Research University, Paris Cedex 05, France.
² Equipe de Chimie Moléculaire, Laboratoire GBCM, EA7528, Conservatoire National des Arts et Métiers, HESAM Université, 2 rue Conté, 75003, Paris, France.

Abstract

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 dihydroartemisinic 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.

Keywords: Amorphadiene; Artemisinin; Elimination; Malaria; Microwaves.