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

O'Neill, P. M., Mukhtar, A., Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192, Bickley, J. F., Davies, Jill, Bachi, M. D. and Stocks, Paul A. (2004) 'Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore [Letter]'. Organic Letters, Vol 6, Issue 18, pp. 3035-3038.

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: antimalarial yingzhaosu bicyclic peroxides licochalcone-a monoterpenes derivatives agent
Subjects: QV Pharmacology > Anti-Inflammatory Agents. Anti-Infective Agents. Antineoplastic Agents > QV 256 Antimalarials
QV Pharmacology > QV 34 Experimental pharmacology (General)
Faculty: Department: Groups (2002 - 2012) > Molecular & Biochemical Parasitology Group
Digital Object Identifer (DOI): https://doi.org/10.1021/ol0492142
Depositing User: Ms Julia Martin
Date Deposited: 21 Feb 2012 10:10
Last Modified: 06 Feb 2018 13:03
URI: http://archive.lstmed.ac.uk/id/eprint/2212

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