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.

Figure optionsDownload as PowerPoint slide