Bioorganic & Medicinal Chemistry Letters 2008-03-01

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

Gemma L Ellis, Richard Amewu, Charlotte Hall, Karen Rimmer, Steven A Ward, Paul M O'Neill

Index: Bioorg. Med. Chem. Lett. 18(5) , 1720-4, (2008)

Full Text: HTML

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.