Intramolecular Additions of Various π-Nucleophiles to Chemoselectively Activated Amides and Application to the Synthesis of (±)-Tashiromine

G Bélanger, R Larouche-Gauthier…

Index: Belanger, Guillaume; Larouche-Gauthier, Robin; Menard, Frederic; Nantel, Miguel; Barabe, Francis Journal of Organic Chemistry, 2006 , vol. 71, # 2 p. 704 - 712

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Citation Number: 45

Abstract

Vilsmeier-Haack type cyclizations proved to be particularly efficient for generating parts of the polycyclic cores of many alkaloids, although only monocyclizations have so far been reported. With the goal of rapidly and efficiently constructing polycyclic alkaloids, we decided to exploit the Vilsmeier-Haack reaction by utilizing iminium ions successively generated and trapped with tethered nucleophiles. To develop such a strategy, we had to set the first ...