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Diastereoselective Three-Component Vinylogous Mannich Reaction
P. Hermange, M. E. T. H. Dau, P. Retailleau, R. H. Dodd*
Institut de Chimie des Substances Naturelles, Gif-sur-Yvette, France
20 November 2009 (online)
Tetrahydroisoquinolines and 1,2-dihydroisoquinolines represent the core structure of various alkaloids and pharmaceutical products. Continuing efforts have focused on gaining access to the optically pure C1-substituted derivatives. The authors report a three-component vinylogous Mannich reaction of an isoquinoline, a silyloxyfuran, and an acyl or sulfonyl chloride to obtain a variety of isoquinolinobutyrolactones in excellent yields and diastereoselectivities. The products can be further utilized to synthesize the core structure of emetine, an antitumor alkaloid.