Tetrahedron

Synthesis of 3-(arylmethylene) isoindolin-1-ones from ynamides by Heck–Suzuki–Miyaura domino reactions. Application to the synthesis of lennoxamine

S Couty, B Liegault, C Meyer, J Cossy

Index: Couty, Sylvain; Liegault, Benoit; Meyer, Christophe; Cossy, Janine Tetrahedron, 2006 , vol. 62, # 16 p. 3882 - 3895

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Citation Number: 81

Abstract

Substituted 3-(arylmethylene) isoindolin-1-ones can be efficiently synthesized from various ynamides and boronic acids by palladium-catalyzed Heck–Suzuki–Miyaura domino reactions. This methodology has been applied to the total synthesis of lennoxamine and a concise route to this isoindolobenzazepine alkaloid was achieved in eight steps from 2, 3- dimethoxybenzoic acid via a key intermediate ynamide.