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

RIVEIRA, M. J.; LA-VENIA, A.; MISCHNE, M. P.

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Utah; Año: 2008 vol. 73 p. 8678 - 8681

0022-3263

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.