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    
Abstract/OtherAbstract:
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.
Authors:
James E Tarver; Madeleine M Joullié
Related Documents :
22395179 - A portable and integrated nucleic acid amplification microfluidic chip for identifying ...
15862319 - Substrate specificity and preference of delta6-desaturase of mucor rouxii.
7194699 - Applications of deuterium labeling in the study of the in vitro conversion of delta 1-p...
6892859 - Studies directed toward synthesis of quassinoids vii. conversion of chenodeoxycholic ac...
11171159 - Cloning and functional expression of the first plant fatty acid elongase specific for d...
15733729 - Regulatory role of peroxisome proliferator-activated receptor delta (ppar delta) in mus...
20018209 - The key roles of elongases and desaturases in mammalian fatty acid metabolism: insights...
7033899 - Studies on elastic tissue of aorta in aortic dissections and marfan syndrome.
1274919 - Serum bile acids in alcoholic liver disease. comparison with histological features of t...
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    
Affiliation:
Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemical synthesis*,  chemistry
Isomerism
Lactones / chemistry*
Oligopeptides / chemistry
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Lactones; 0/Oligopeptides; 0/cyclomarin A

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


Previous Document:  Facile syntheses of oxazolines and thiazolines with N-acylbenzotriazoles under microwave irradiation...
Next Document:  Straightforward asymmetric entry to highly functionalized 3-substituted 3-hydroxy-beta-lactams via B...