| Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone. | |
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MedLine Citation:
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PMID: 19514728 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Cara Cesario; Marvin J Miller |
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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 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 74 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2009 Aug |
Date Detail:
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Created Date: 2009-09-03 Completed Date: 2009-12-08 Revised Date: 2013-06-02 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5730-3 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Azetidines
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chemistry* Indium / chemistry* Molecular Structure Palladium / chemistry* Pyrimidine Nucleosides / chemical synthesis*, chemistry Stereoisomerism Uracil / analogs & derivatives*, chemical synthesis, chemistry |
| Grant Support | |
ID/Acronym/Agency:
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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:
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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 | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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