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    
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.
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:  2014-09-16    
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    
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MeSH Terms
Azetidines / chemistry*
Indium / chemistry*
Molecular Structure
Palladium / chemistry*
Pyrimidine Nucleosides / chemical synthesis*,  chemistry
Uracil / analogs & derivatives*,  chemical synthesis,  chemistry
Grant Support
GM068012/GM/NIGMS NIH HHS; R01 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
Reg. No./Substance:
0/4-acetoxy-2-azetidinone; 0/Azetidines; 0/Pyrimidine Nucleosides; 0/uracil polyoxin C; 045A6V3VFX/Indium; 56HH86ZVCT/Uracil; 5TWQ1V240M/Palladium

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

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