The Journal of Organic Chemistry · 2007 · 63 citations · 44 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryMicrowave-assisted SynthesisNatural Product Drug DiscoveryOrganic SynthesisRetrosynthetic AnalysisIsoquinoline ChemistryIsoquinoline SynthesisMicrowave Irradiation EffectsMicrowave-assisted CatalysisMicrowave-assisted Condensation ReactionsMicrowave-assisted Heterocycle SynthesisMicrowave-assisted Organic SynthesisNatural Product Total Synthesis
Rapid and efficient [2 + 2 + 2] cyclotrimerization reactions were discovered through the application of microwave irradiation in conjunction with a Ni(CO)(2)(PPh(3))(2) catalyst. This enables the facile construction of highly substituted indane, isoindoline, and tetraline core structures. The developed microwave-mediated Ni-catalyzed cyclotrimerization reaction was employed as the key step in a concise synthesis of the isoquinoline natural product illudinine. This represents the first example of a Ni-catalyzed cyclotrimerization reaction in total synthesis.
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