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New Strategy for the Construction of Epoxy-Bridged Tetrahydropyran Frameworks from Trioxane Precursors: Application to a Concise Synthesis of a Riesling Acetal

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journal contribution
posted on 07.11.2008, 00:00 by Martín J. Riveira, Agustina La-Venia, Mirta P. Mischne
A simple one-pot method to prepare dioxabicyclo[2.2.1] heptane derivatives, from readily available 1,2,4-trioxane frameworks, under catalytic hydrogenation conditions over a platinum surface is reported. The overall transformation involves the hydrogenation of the double bond and a ring contraction rearrangement that presumably proceeds via a hydrogenolytic cleavage of the O−O bond and subsequent intramolecular ketalization. The strategy was successfully applied to the synthesis of a Riesling acetal.