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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 3 , 2006

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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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Article Details

Year: 2006
Page: [247 - 249]
Pages: 3
DOI: 10.2174/157017806775789903
Price: $65

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