Divergent and Modular Synthesis of Terpenoid Scaffolds via a AuI Catalyzed One-Pot Cascade
Huy Tran
Department of Chemistry and Biomolecular Sciences, Centre for Catalysis, Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N6N5 Canada
Search for more papers by this authorDr. Guillaume Revol
OmegaChem, 480 Rue Perreault, Saint-Romuald, Quebec, G6W7V6 Canada
Search for more papers by this authorAlyson Poyser
Transport Canada, 330 Sparks St., Ottawa, ON, K1A0N8 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Louis Barriault
Department of Chemistry and Biomolecular Sciences, Centre for Catalysis, Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N6N5 Canada
Search for more papers by this authorHuy Tran
Department of Chemistry and Biomolecular Sciences, Centre for Catalysis, Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N6N5 Canada
Search for more papers by this authorDr. Guillaume Revol
OmegaChem, 480 Rue Perreault, Saint-Romuald, Quebec, G6W7V6 Canada
Search for more papers by this authorAlyson Poyser
Transport Canada, 330 Sparks St., Ottawa, ON, K1A0N8 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Louis Barriault
Department of Chemistry and Biomolecular Sciences, Centre for Catalysis, Research and Innovation, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N6N5 Canada
Search for more papers by this authorGraphical Abstract
A one-pot sequence involving an exo-Diels–Alder reaction followed by a Lewis acid gold(I) catalyzed cyclization has allowed access to three complex polycyclic scaffolds. Structural diversity is obtained by varying solvent and the ligand of the gold(I) catalyst. An additional Diels–Alder step generates tetracyclic cores possessing up to 5 stereocenters.
Abstract
A one-pot cascade sequence to generate synthetically challenging polycyclic scaffolds is reported utilizing a novel Lewis acid gold catalyst for the key cyclization step, enabling the divergent synthesis of both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores through both ligand and reaction condition control. We have combined the intrinsic complexity and stereoselectivity of cycloadditions with the electronic and steric properties of gold complexes to selectively generate complex polycyclic scaffolds in a single operation.
Conflict of interest
The authors declare no conflict of interest.
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