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 S(N)2' reaction and an intramolecular oxa-Michael addition has been developed by treating Morita-Baylis-Hillman acetates of nitroalkenes with arenols, such as beta-naphthols, alpha-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. (C) 2013 Elsevier Ltd. All rights reserved.