INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 3-CARBOMETHOXY-2-PYRONES. CONTROLLED INTRODUCTION OF OXYGENATED AROMATICS: BENZENE, PHENOL, CATECHOL, RESORCINOL, PYROGALLOL ANNULATION.

Article abstract of DOI:10.1016/S0040-4039(01)99816-8

Implementation of one of four inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones with N-vinyl-2-pyrrolidinone, vinylene carbonate, 1,1-dimethoxy-ethylene or 1,1,2-trimethoxyethylene followed by choice of two standard reaction sequences: (1) removal of the carbomethoxy group (NaOH: copper powder, quinoline , Δ) or (2) its conversion to an acetate allows the preparation of a full range of oxygen substituted aromatics from a single intermediate and represent methods of benzene, 1-, 2- or 3-phenol , symmetrical or unsymmetrical catechol, resorcinol and pyrogallol annulation.