Synthesis of Benzodioxane and Benzofuran Scaffolds Found in Neolignans via TMS Triflate Mediated Addition to 1,4-Benzo­dioxane Hemiacetals

Abstract

This research reports the successful asymmetric synthesis of both a 9-hydroxy-5′-methoxy-1,4-benzodioxane framework and a highly functionalised benzofuran scaffold. Both synthetically desirable structures are the result of a Lewis acid catalysed addition of an aryl nucleophile to 1,4-benzodioxane hemiacetals and offer a route towards the synthesis of a number of naturally occurring neolignans.

Key words

lignin - 1,4-benzodioxane - benzofuran - asymmetric synthesis - hemiacetal - oxonium - Mitsunobu reaction

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