Document Detail


Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone.
MedLine Citation:
PMID:  19514728     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Carbocyclic uracil polyoxin C analogs are prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct in fewer than nine steps. Pd(0)/InI-mediated allylation of 4-acetoxy-2-azetidinone is used to install the beta-amino acid side chain at the C-5' position of the carbocycle.
Authors:
Cara Cesario; Marvin J Miller
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Aug 
Date Detail:
Created Date:  2009-09-03     Completed Date:  2009-12-08     Revised Date:  2013-06-02    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5730-3     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556, USA.
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MeSH Terms
Descriptor/Qualifier:
Azetidines / chemistry*
Indium / chemistry*
Molecular Structure
Palladium / chemistry*
Pyrimidine Nucleosides / chemical synthesis*,  chemistry
Stereoisomerism
Uracil / analogs & derivatives*,  chemical synthesis,  chemistry
Grant Support
ID/Acronym/Agency:
GM068012/GM/NIGMS NIH HHS; R01 GM068012-02/GM/NIGMS NIH HHS; R01 GM068012-03/GM/NIGMS NIH HHS; R01 GM068012-04/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/4-acetoxy-2-azetidinone; 0/Azetidines; 0/Pyrimidine Nucleosides; 0/uracil polyoxin C; 66-22-8/Uracil; 7440-05-3/Palladium; 7440-74-6/Indium
Comments/Corrections

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