nBu4NPF6 mediated highly regioselective synthesis of functionally embellished naphthofurans has been achieved from easily available naphthols and propargyl alcohols through a cascade benzylation, oxacyclisation (5-exo dig) and isomerization under solvent free conditions. The reaction works in a short time through dibenzyl ether formation followed by the decomposition to the carbocation to furnish the high yielding products with large substrate scope. The synthetic utility of the products is demonstrated through C(sp3)-H functionalization. In addition, we investigated selected naphthofurans for their anti-amyloidogenic properties. Preliminary studies suggest that these are excellent inhibitors for amyloid formation, a hallmark for several neurodegenerative diseases.
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© 2016 The Royal Society of Chemistry.