Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore

Organic Letters
Paul M O'NeillPaul A Stocks

Abstract

[reaction: see text] Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates alpha-hydroxyperoxides that can be condensed in situ with various ketones to afford a series of functionalized 1,2,4-trioxanes in good yields. Manipulation of the phenylsulfenyl group in 4a allows for convenient modification to the spiro-trioxane substituents, and we describe, for the first time, the preparation of a new class of antimalarial prodrug.

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Citations

Jan 5, 2014·Chemical Reviews·Fabrice DénèsPhilippe Renaud
Nov 21, 2012·Journal of Medicinal Chemistry·Chandan SinghRuchir Kant
Dec 14, 2012·Future Medicinal Chemistry·Sumit S MahajanAdam R Renslo
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Aug 9, 2021·Bioorganic & Medicinal Chemistry Letters·Monika ShuklaVed Prakash Verma

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Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.

Antimalarial Agents

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.