Oxidant free one-pot transformation of bio-based 2,5-bis-hydroxymethylfuran into α-6-hydroxy-6-methyl-4-enyl-2H-pyran-3-one in water

•The bio-based 2,5-hydroxymethylfuran is transformed into a pyranone derivative.•Pyranones are useful synthons for the preparation of biologically active compounds.•Amberlyst 15® is employed as an environmental friendly recoverable and recyclable acid catalyst.•The reaction is selective and occurs under mild conditions in water.•Reaction conditions are greener than those usually employed for the synthesis of pyranones.

A new synthetic route for obtaining α-6-hydroxy-6-methyl-4-enyl-2H-pyran-3-one, a useful synthon for the preparation of biologically active compounds, has been developed from the bio-based platform derivative (2,5-bis-hydroxymethylfuran) BHMF. The reaction occurs with good selectivity in water, under mild conditions and employing an heterogeneous recyclable acid (Amberlyst 15®) as catalyst, avoiding the use of oxidizing agents. The reaction provides access to poly-oxygenated compounds characterized by a molecular motif commonly found in many natural products.

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