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

Mario Andrés Gómez Fernández | Zendy; Marllon Nascimento de Oliveira | Zendy; Andrea Zanetti | Zendy; Geoffrey Schwertz | Zendy; Janine Cossy | Zendy; Zacharias Amara | Zendy

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

Author(s) -

Mario Andrés Gómez Fernández,

Marllon Nascimento de Oliveira,

Andrea Zanetti,

Geoffrey Schwertz,

Janine Cossy,

Zacharias Amara

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c00636

Subject(s) - chemistry , artemisinin , aldehyde , thioether , photocatalysis , combinatorial chemistry , photooxygenation , menthol , photochemistry , catalysis , organic chemistry , plasmodium falciparum , singlet oxygen , malaria , immunology , biology , oxygen

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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