Document Detail

Synthesis of gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids from fragmentation of gamma- and delta-lactones.
MedLine Citation:
PMID:  14750809     Owner:  NLM     Status:  MEDLINE    
A noncoded amino acid of cyclomarin A (1) was synthesized in a racemic fashion. The method employs a six-membered ring template to control the relative stereochemistry and introduction of the functional groups. Ultimately, Pd-catalyzed fragmentation of the lactone provided gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids. A Pd-catalyzed ring opening of a gamma-lactone is also reported.
James E Tarver; Madeleine M Joullié
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Feb 
Date Detail:
Created Date:  2004-01-30     Completed Date:  2004-05-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  815-20     Citation Subset:  IM    
Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry
Lactones / chemistry*
Oligopeptides / chemistry
Reg. No./Substance:
0/Amino Acids; 0/Lactones; 0/Oligopeptides; 0/cyclomarin A

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