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Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence


  • This work was supported by the Technical University of Denmark, the Danish Council for Strategic Research, the Danish Council for Independent Research, Natural Sciences, Technology and Production Sciences, the Lundbeck Foundation, the Carlsberg Foundation, and the Torkil Holm Foundation. We thank Prof. David Tanner for valuable discussions.


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Tandem bicycle: In the title reaction double bonds created during ring-closing metathesis isomerize to generate reactive iminium intermediates that undergo intramolecular cyclization reactions with tethered heteroatom and carbon nucleophiles. In this way, a series of biologically interesting heterocyclic compounds can be made, including a known precursor for the total synthesis of the antiparasitic natural product harmicine.