Title of article :
Synthetic Approaches to Polar Antimalarial 1,2,4-Trioxanes from C5-Aldehyde and Ipsdienol
Author/Authors :
Griesbeck, Axel G. University of Cologne - Institute of Organic Chemistry, Germany , Höinck, Oliver University of Cologne - Institute of Organic Chemistry, Germany , Lex, Johann University of Cologne - Institute of Organic Chemistry, Germany
Abstract :
The 4-acetoxy-substituted tiglic aldehyde (C5-aldehyde) 1 is unreactive under singlet oxygen photooxygenation conditions. When converted into the corresponding ester-alcohol 3, the photooxygenationled to an allylic hydroperoxide 4 which was converted into a series of 1,2,4-trioxanes 5 by BF3-catalyzedperoxyacetalization. A similar approach to polar peroxides started from the terpene alcohol ipsdienol and offered a new route to mixed trioxane-endoperoxides 11.
Keywords :
Photooxygenation , ipsdienol , peroxyacetalization , antimalarial trioxanes
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
