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

作者：Riveira Martin J; La Venia Agustina; Mischne Mirta P^*

来源：Journal of Organic Chemistry, 2008, 73(21): 8678-8681.

DOI：10.1021/jo8017928

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.

• 出版日期2008-11-7