Abstract Submission Form
Inorganic Chemistry Exchange Conference
August 20 & 21, 2015
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Example of complete abstract submission for QOMSBOC 2013
OR03 Total synthesis of Virosine A using one pot sequential Vilsmeier16
Haack and Mannich cyclizations
Marianne Dupuis, Robin Larouche-Gauthier and Guillaume Bélanger* Département de chimie,
Université de Sherbrooke, Sherbrooke, QC, J1K 2R1, Guillaume.Belanger@USherbrooke.ca
Securinega alkaloids are known to act on the central nervous system as -aminobutyric acid
receptor antagonists. A member of this family, Virosine A, was isolated in 2008 and shows an
uncommon quinolizidine skeleton fused to an azabicyclo[2.2.2]octane subunit. As part of our
research program aimed at developing new cascade and sequential reactions towards the
construction of architecturally complex natural products, we reported the first total synthesis
Virosine A. The key step features a Vilsmeier-Haack cyclization (amide activation and trapping
with a non-aromatic carbon -nucleophile) that is coupled to a Mannich reaction to form two CC bonds and two cycles in a single transformation. The tetracyclic natural product was
obtained in only 13 steps, in high enantiomeric purity, highlighting the efficiency of our
sequential cyclization strategy.1
1. Bélanger,* G.; Dupuis, M.; Larouche-Gauthier, R. J. Org. Chem. 2012, 77, 3215-3221