| An oxidopyrylium cyclization/ring-opening route to polysubstituted α-hydroxytropolones. | |
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MedLine Citation:
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PMID: 23167954 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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α-Hydroxytropolones are a class of molecules with therapeutic potential against several human diseases. However, structure-activity relationship studies on these molecules have been limited due to a scarcity of efficient synthetic methods to access them. It is demonstrated herein that α-hydroxytropolones can be generated through a BCl(3)-mediated ring-opening/aromatization/demethylation process on 8-oxabicyclo[3.2.1]octenes. Used in conjunction with an improved method based on established oxidopyrylium dipolar cycloadditions, several polysubstituted α-hydroxytropolones can be accessed in three steps from readily available α-hydroxy-γ-pyrones. |
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Authors:
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Christine Meck; Noushad Mohd; Ryan P Murelli |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2012-11-20 |
Journal Detail:
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Title: Organic letters Volume: 14 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2012 Dec |
Date Detail:
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Created Date: 2012-12-11 Completed Date: 2013-02-22 Revised Date: 2013-04-16 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 5988-91 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Brooklyn College, The City University of New York, Brooklyn, New York 11210, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Cyclization Humans Molecular Structure Stereoisomerism Structure-Activity Relationship Tropolone / analogs & derivatives*, chemical synthesis*, chemistry |
| Grant Support | |
ID/Acronym/Agency:
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SC2GM099596/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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533-75-5/Tropolone |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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