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

Paul M O'Neill Amira Mukhtar Stephen A Ward Jamie F Bickley Jill Davies Mario D Bachi Paul A Stocks

Org Lett

Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, UK.

Published: September 2004

[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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http://dx.doi.org/10.1021/ol0492142DOI Listing

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