Regiospecific synthesis of arenofurans via cascade reactions of arenols with Morita–Baylis–Hillman acetates of nitroalkenes and total synthesis of isoparvifuran

A cascade process involving an SN2′ reaction and an intramolecular oxa-Michael addition has been developed by treating Morita–Baylis–Hillman acetates of nitroalkenes with arenols, such as β-naphthols, α-naphthols, and substituted phenols under basic conditions. The products, arenofurans, are formed as single regioisomers in good to excellent yield in most cases. The methodology has been successfully employed for the total synthesis of an anti fungal agent isoparvifuran. [Display omitted]