The versatility of furfuryl alcohols and furanoxonium ions in synthesis?

Chemical Communications Pub Date: 2014-04-02 DOI: 10.1039/C4CC01196A

Abstract

Substituted furfuryl alcohols are extraordinarily versatile starting materials in synthesis. They are precursors to furanoxonium ion intermediates which are implicated in the Piancatelli reaction (leading to 2-cyclopentenones) and in the synthesis of novel dihydrofuran-based exo enol ether/cyclic ketal natural products. They are also intermediates in a recently discovered (4+3) cycloaddition reaction with 1,3-dienes leading to furan ring-fused cycloheptenes. Here we provide a perspective on recent developments in these areas of synthesis, alongside recent applications of the Achmatowicz reaction and [5+2] cycloaddition reactions of the resulting oxidopyrylium ions.

Graphical abstract: The versatility of furfuryl alcohols and furanoxonium ions in synthesis
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