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

A new synthetic route for obtaining alpha-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 (R)) 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. (C) 2015 Elsevier B.V. All rights reserved.