4.8 Article

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

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ORGANIC LETTERS
卷 23, 期 15, 页码 5593-5598

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00636

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  1. Bill & Melinda Gates Foundation [OPP1190174]
  2. Bill and Melinda Gates Foundation [OPP1190174] Funding Source: Bill and Melinda Gates Foundation

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A new method for the preparation of artemisinin was reported based on selective photochemical hydrothiolation of amorphadiene. Two distinctive activation pathways were discovered under solvent-free conditions or using a photocatalyst promoting H-abstraction. The key intermediate dihydroartemisinic aldehyde in the synthesis of artemisinin was obtained through chemoselective oxidation of the photochemically generated thioether followed by Pummerer rearrangement.
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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