New strategy for the construction of epoxy-bridged tetrahydropyran frameworks from trioxane precursors: application to a concise synthesis of a Riesling acetal.
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.
Riveira
Martín J
MJ
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas-Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
La-Venia
Agustina
A
Mischne
Mirta P
MP
D000080:Acetals / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D004852:Epoxy Compounds / Q000737:chemistry; D006536:Heptanes / Q000138:chemical synthesis; D011714:Pyrans / Q000737:chemistry*
D000080:Acetals; D001643:Bridged Bicyclo Compounds; D004852:Epoxy Compounds; D006536:Heptanes; D011714:Pyrans