Synthesis of (±)??Glaucine and (±)??Neospirodienone via an One??Pot Bischler Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent
Abstract Condensation of 3, 4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, ie, 4a–e, via a practical and efficient one-pot Bischler–Napieralski reaction, followed by NaBH 4 reduction, produced a series of 1-benzyl-1, 2, 3, 4- tetrahydroisoquinolines, ie, 5a–e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a–e of the latter with hypervalent iodine ([IPh (CF 3 COO ...
