Synthetic Approaches to Polar Antimalarial 1,2,4-Trioxanes from C5-Aldehyde and Ipsdienol

Axel   G.   Griesbeck; Oliver      Hoinck; Johann      Lex

doi:10.2174/157017806775789903

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 photooxygenation led to an allylic hydroperoxide 4 which was converted into a series of 1,2,4-trioxanes 5 by BF3-catalyzed peroxyacetalization. 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

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Letters in Organic Chemistry

Title: Synthetic Approaches to Polar Antimalarial 1,2,4-Trioxanes from C5-Aldehyde and Ipsdienol

Volume: 3 Issue: 3

Author(s): Axel G. Griesbeck, Oliver Hoinck and Johann Lex

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Keywords: Photooxygenation, ipsdienol, peroxyacetalization, antimalarial trioxanes

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 photooxygenation led to an allylic hydroperoxide 4 which was converted into a series of 1,2,4-trioxanes 5 by BF3-catalyzed peroxyacetalization. A similar approach to polar peroxides started from the terpene alcohol ipsdienol and offered a new route to mixed trioxane-endoperoxides 11.

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Griesbeck G. Axel, Hoinck Oliver and Lex Johann, Synthetic Approaches to Polar Antimalarial 1,2,4-Trioxanes from C5-Aldehyde and Ipsdienol, Letters in Organic Chemistry 2006; 3 (3) . https://dx.doi.org/10.2174/157017806775789903