Document Detail


3-Aryltetronic acids: efficient preparation and use as precursors for vulpinic acids.
MedLine Citation:
PMID:  19102655     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphenyl)tetronic acid in three steps involving the reaction of the corresponding dianion with an alpha-ketoester and the dehydration of the tertiary alcohols obtained into mixtures of (E)- and (Z)-alkenes, which were converted under UV irradiation at 254 nm to natural (E)-isomers. Syntheses of pinastric acid, 4,4'-dimethoxyvulpinic acid, and the first synthesis of recently isolated methyl 3',5'-dichloro-4,4'-di-O-methylatromentate were hence achieved in an efficient manner.
Authors:
Aurélie Mallinger; Thierry Le Gall; Charles Mioskowski
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2009-01-30     Completed Date:  2009-06-23     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1124-9     Citation Subset:  IM    
Affiliation:
CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, Bat. 547, 91191 Gif-sur-Yvette, France.
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MeSH Terms
Descriptor/Qualifier:
Acetates / chemistry
Butanols / chemistry
Furans / chemical synthesis*,  chemistry
Phenylacetates / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Acetates; 0/Butanols; 0/Furans; 0/Phenylacetates; 4971-56-6/tetronic acid; 73622-57-8/vulpinic acid; 865-47-4/tert-butoxide, potassium

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


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