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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Intermolecular Oxidopyrylium (5 + 2) Cycloaddition/Reductive Ring-Opening Strategy for the Synthesis of
Orugbani S Eli1,2, Lauren P Bejcek1,2, Anastasiya Lyubimova1,2
1Department of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.
Abstract:
α-Methoxytropone is a structural motif found in various natural products and other compounds of interest to the scientific community but remains a synthetic challenge. The present Note describes the synthesis of variously substituted α-methoxytropones and related compounds through an intermolecular 3-hydroxy-4-pyrone-based oxidopyrylium (5 + 2) cycloaddition followed by a samarium iodide-mediated reductive ring-opening. The strategy is highlighted in the synthesis of a novel AC-ring analogue of colchicine to compare it to existing methods.
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