Photochemical Hydrothiolation of Amorphadiene and Formal Synthesis of Artemisinin via a Pummerer Rearrangement - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2021

Photochemical Hydrothiolation of Amorphadiene and Formal Synthesis of Artemisinin via a Pummerer Rearrangement

Résumé

A new access to artemisinin is reported based on a selective photochemical hydrothiolation of amorphadiene, a waste product of the industrial semisynthetic route. This study highlights the discovery of two distinctive activation pathways under solvent-free conditions or using a photocatalyst promoting H-abstraction. Subsequently, a chemoselective oxidation of the resulting photochemically generated thioether, followed by a Pummerer rearrangement, affords dihydroartemisinic aldehyde, a key intermediate in the synthesis of artemisinin.
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Dates et versions

hal-03407621 , version 1 (11-03-2022)

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Mario Andrés Gomez Fernandez, Marllon Nascimento de Oliveira, Andrea Zanetti, Geoffrey Schwertz, Janine Cossy, et al.. Photochemical Hydrothiolation of Amorphadiene and Formal Synthesis of Artemisinin via a Pummerer Rearrangement. Organic Letters, 2021, 23 (15), pp.5593-5598. ⟨10.1021/acs.orglett.1c00636⟩. ⟨hal-03407621⟩
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