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  • An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity.

An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity.

Bioorganic & medicinal chemistry letters (2008-02-05)
Gemma L Ellis, Richard Amewu, Charlotte Hall, Karen Rimmer, Steven A Ward, Paul M O'Neill
ABSTRACT

Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H(2)O(2) and catalytic I(2) to form the gem-dihydroperoxide followed by a Ag(2)O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized.

MATERIALS
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Product Description

Sigma-Aldrich
1,3-Diiodopropane, 99%, contains copper as stabilizer