Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore |
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Authors: | O'Neill Paul M Mukhtar Amira Ward Stephen A Bickley Jamie F Davies Jill Bachi Mario D Stocks Paul A |
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Affiliation: | Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, UK. p.m.oneill01@liv.ac.uk |
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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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