Synthesis

A Concise Synthesis of 3-Arylated Di-and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

S Lebrun, A Couture, E Deniau, P Grandclaudon

Index: Lebrun, Stephane; Couture, Axel; Deniau, Eric; Grandclaudon, Pierre Synthesis, 2012 , vol. 44, # 9 p. 1410 - 1416

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Citation Number: 11

Abstract

Abstract A variety of 3-arylated di-and tetrahydro-2 H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki–Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1, 3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a ...