Document Detail


Synthesis of bicyclic tertiary alpha-amino acids.
MedLine Citation:
PMID:  17168622     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.
Authors:
Jon-Paul Strachan; Regina C Whitaker; Craig H Miller; Balwinder S Bhatti
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  71     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2006 Dec 
Date Detail:
Created Date:  2006-12-15     Completed Date:  2007-02-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9909-11     Citation Subset:  IM    
Affiliation:
Targacept, Inc., Winston-Salem, North Carolina 27101-4165, USA.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemical synthesis*,  chemistry
Bicyclo Compounds / chemical synthesis*,  chemistry
Carboxylic Acids / chemical synthesis,  chemistry
Molecular Structure
Stereoisomerism
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Bicyclo Compounds; 0/Carboxylic Acids

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