Document Detail


Mild construction of 3-methyl tetramic acids enabling a formal synthesis of palau'imide.
MedLine Citation:
PMID:  22804621     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A general method to construct 3-methyl-4-O-methylated tetramic acids displaying a C-5 stereocenter is presented. The synthetic sequence employs a SmI(2)-mediated cyclization, whereby the chirality of the emerging tetramic acid core is retained from the starting chiral amino acid. Application to palau'imide is discussed.
Authors:
Wen-Ju Bai; Stephen K Jackson; Thomas R R Pettus
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-07-17
Journal Detail:
Title:  Organic letters     Volume:  14     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Aug 
Date Detail:
Created Date:  2012-08-03     Completed Date:  2012-12-07     Revised Date:  2014-10-09    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3862-5     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry*
Combinatorial Chemistry Techniques
Cyanobacteria / chemistry
Cyclization
Molecular Structure
Oligopeptides / chemical synthesis*,  chemistry
Pyrroles / chemical synthesis*,  chemistry
Pyrrolidinones / chemical synthesis*,  chemistry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM064831/GM/NIGMS NIH HHS; R01 GM064831/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Oligopeptides; 0/Pyrroles; 0/Pyrrolidinones; 0/palau'imide; 503-83-3/tetramic acid

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


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