Synthesis of (±)??Glaucine and (±)??Neospirodienone via an One??Pot Bischler Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

WJ Huang, OV Singh, CH Chen…

Index: Huang, Wei-Jan; Singh, Om V.; Chen, Chung-Hsiung; Lee, Shoei-Sheng Helvetica Chimica Acta, 2004 , vol. 87, # 1 p. 167 - 174

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Citation Number: 25

Abstract

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 ...