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1-Aryltetralin privileged structure-based libraries: parallel synthesis of N-aryl and N-biaryl γ-lactam lignans
Authors:Matthieu Dorbec  Claude Monneret  Emmanuel Bertounesque
Institution:a UMR 176 CNRS-Institut Curie, Centre de Recherche, 26 rue d'Ulm, 75248 Paris Cedex 05, France
b Département de RMN, Ecole Nationale Supérieure de Chimie de Paris, 11 rue P. et M. Curie, 75231 Paris Cedex 05, France
Abstract:The parallel solution-phase synthesis of two libraries of product-like compounds derived from a 1-aryltetralin privileged structure is described. The N-aryl picropodophyllone γ-lactams were synthesized from methyl ester thuriferic acid via InCl3-tandem aza-Michael addition-cyclization reaction of anilines. Bromo-aryl compounds from this library were subjected to a ligandless palladium Suzuki cross-coupling to give the expected N-biaryl picropodophyllin γ-lactams.
Keywords:Biaryls  Lactam lignans  Privileged structure  Tandem reaction  InCl3  Ligandless Suzuki reaction  Parallel solution-phase synthesis
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