Michael D. Mullican

Synthetic analgesics: preparation of racemic 6,7-benzomorphans

Abstract A simple preparation of 2-carbomethoxy-2-azabicyclo[3.3.1]nonan-6-one ( 7 and its conversion to the racemic benzomorphans: 9 , 10 , 14 are described.

Inverse electron demand diels-alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, pyrogallol annulation.

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-dimethoxyethylene 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 [NaOH: (CO)2Cl2: (CH3)2CuLi: m-CPBA] 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.

Inverse electron demand diels-alder reaction of 3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene: a simple and mild method of aryl annulation

Abstract A simple process for aryl annulation based on the inverse electron demand Diels-Alder reaction of 5,6-substituted-3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene is described.