Intermolecular Oxidopyrylium (5 + 2) Cycloaddition/Reductive Ring-Opening Strategy for the Synthesis of α-Methoxytropones.

Orugbani S Eli, Lauren P Bejcek, Anastasiya Lyubimova, Dan L Sackett, Ryan P Murelli

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Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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1 citing paper in PubMed.

Deconstruction of Desacetamidocolchicine's B Ring Reveals a Class 3 Atropisomeric AC Ring with Tubulin Binding Properties.The Journal of organic chemistry · 2025
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5 · Who and what money

Authors and funding

5 authors.

Orugbani S EliDepartment of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.

Lauren P BejcekDepartment of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.

Anastasiya LyubimovaDepartment of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.

Dan L SackettDivision of Basic and Translational Biophysics, Eunice Kennedy Shriver National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, Maryland 20892, United States.

Ryan P MurelliDepartment of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, United States.ORCID 0000-0002-4247-3936

Funding

Development and Exploitation of New Synthetic Strategies for TropolonesSC1GM111158 · NIGMS · BROOKLYN COLLEGE · PI MURELLI, RYAN · 2015 to 2023

$3.1M

NIGMS NIH HHS SC1 GM111158

6 · The paper itself

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.

Identifiers

PMID39529545

DOI10.1021/acs.joc.4c01989

PMCPMC11629294

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