Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products
Philip H. Gilmartin, Marisa C. Kozlowski
Abstract
A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.
Topics & Concepts
Intramolecular forceChemistryPhenolPhenolsCatalysisVanadiumOxidative coupling of methaneOrganic chemistryCombinatorial chemistryAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloids