Document Detail


An oxidopyrylium cyclization/ring-opening route to polysubstituted α-hydroxytropolones.
MedLine Citation:
PMID:  23167954     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Christine Meck; Noushad Mohd; Ryan P Murelli
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2012-11-20
Journal Detail:
Title:  Organic letters     Volume:  14     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Dec 
Date Detail:
Created Date:  2012-12-11     Completed Date:  2013-02-22     Revised Date:  2013-12-12    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5988-91     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Cyclization
Humans
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
Tropolone / analogs & derivatives*,  chemical synthesis*,  chemistry
Grant Support
ID/Acronym/Agency:
SC2 GM099596/GM/NIGMS NIH HHS; SC2GM099596/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
7L6DL16P1T/Tropolone
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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