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AuthorBélanger, Guillaume (7)Larouche-Gauthier, Robin (3)Ménard, Frédéric (3)Barabé, Francis (2)Lévesque, François (2)... View MoreSubjectCyclization (6)Ethers (4)Amides (3)Ions (3)Organic compounds (3)... View MorePublication date2008 (2)2007 (1)2006 (2)2005 (2)Types of document
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Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine

Bélanger, Guillaume; Larouche-Gauthier, Robin; Ménard, Frédéric; Nantel, Miguel; Barabé, Francis (2006)
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 ...
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Effect of substitution on the intramolecular 1,3-dipolar cycloaddition of alkene tethered münchnones

Bélanger, Guillaume; April, Myriam; Dauphin, Étienne; Roy, Stéphanie (2007)
Abstract: A sequence of chemoselective activation of N-acylaminoacids, münchnone generation, intramolecular 1,3-dipolar cycloaddition, and ring opening efficiently generated functionalized polycyclic structures such as ...
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Synthesis of the tricyclic core of alkaloid securinol B using a cascade of vilsmeier-haack and mannich cyclizations

Larouche-Gauthier, Robin; Bélanger, Guillaume (2008)
Abstract: The Securinega alkaloids are a family of approximately 20 tetracyclic compounds isolated from diverse Securinega, Phyllanthus, and Margaritaria species of the Euphorbiaceae plant family. Most of these alkaloids ...
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Competition between alkenes in intramolecular ketene-alkene [2 + 2] cycloaddition: What does it take to win?

Bélanger, Guillaume; Lévesque, François; Pâquet, Julie; Barbe, Guillaume (2005)
Abstract: In the course of developing a new synthetic methodology using ketenes in sequential cycloaddition steps, we were faced with a competition problem with molecules containing a ketene tethered to more than one ...
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Highly chemoselective formation of aldehyde enamines under very mild reaction conditions

Bélanger, Guillaume; Doré, Michael; Ménard, Frédéric; Darsigny, Véronique (2006)
Abstract: Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or ...
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Addition of tethered nonaromatic carbon nucleophiles to chemoselectively activated amides

Bélanger, Guillaume; Larouche-Gauthier, Robin; Ménard, Frédéric; Nantel, Miguel; Barabé, Francis (2005)
Abstract: In an effort to develop new ways of synthesizing polycyclic alkaloids, we successfully added silyl enol ethers, allylsilanes, and enamines to iminium ions generated from amides. Because of their higher oxidation ...
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A Versatile cascade of intramolecular vilsmeier-haack and azomethine ylide 1,3-dipolar cycloaddition toward tricyclic cores of alkaloids

Lévesque, François; Bélanger, Guillaume (2008)
Abstract: In the pursuit of synthetic efficiency, we developed an innovative one-pot transformation of linear substrates into bi- and tricyclic adducts using a cascade of amide activation, nucleophilic cyclization, ...

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