Allmendinger, Thomas, Furet, Pascal, Denay, Regis, Kotoni, Dorina, Bixel, Dominique and Anokwah, Daniel K. (2022) 9-epi-Artemisinin - How a single stereo center affects chemical reactivity and activity. Helvetica Chimica Acta. ISSN 0018-019X1522-2675

Abstract

9-Epi-Artemisinin is established as component of Artemisinin from either natural or semisynthetic sources. As a potential by-product, its fate during the preparation of Artemether was investigated showing that it follows a different reaction pathway. Borohydride reduction furnishes the intermediate 9-epi-dihydroartemisinin which rearranges to a peroxo-acetal with unprotected carbonyl moieties. These are further reduced giving rise to soluble hydroxy compounds which do not hamper the quality of Artemether. The different stability of dihydroartemisinin DHA and its 9-epi-isomer are rationalized by steric hindrance and verified by quantum chemical calculations.

Item Type:	Article
Date Deposited:	21 May 2022 00:45
Last Modified:	21 May 2022 00:45
URI:	https://oak.novartis.com/id/eprint/45780