Document Detail

A convenient route to the synthesis of isotopomeric dihydro-2(3H)furanones.
MedLine Citation:
PMID:  17447794     Owner:  NLM     Status:  MEDLINE    
A general synthetic procedure leading to isotopomeric dihydro-2(3H)furanones (gamma-butyrolactones) containing two, four, or six deuterium atoms has been developed. The labeled dihydro-2(3H)furanones were synthesized in quantitative yield from the saturated diacid C4 (succinic) or unsaturated diacids C4 (fumaric, maleic, or acetylendicarboxylic) in the presence of Ru4H4(CO)8(PBu3)4 using a deuterium pressure of 180 bar at 180 degrees C. This methodology was applied to the total synthesis of a hexadeuterated matairesinol lignan: The 3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]dihydro-2(3H)furanone-[7,7',8,8',9',9'-D6] (benzyl-protected matairesinol-D6) was fully characterized.
Piero Frediani; Luca Rosi; Marco Frediani; Gianluca Bartolucci; Massimo Bambagiotti-Alberti
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-04-21
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  55     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2007 May 
Date Detail:
Created Date:  2007-05-09     Completed Date:  2007-08-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3877-83     Citation Subset:  IM    
Department of Organic Chemistry, University of Florence, Sesto, Italy.
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MeSH Terms
4-Butyrolactone / chemistry*
Fumarates / chemistry
Furans / chemical synthesis*
Isotope Labeling / methods*
Lignans / chemical synthesis*
Maleates / chemistry
Succinic Acid / chemistry
Reg. No./Substance:
0/Fumarates; 0/Furans; 0/Lignans; 0/Maleates; 110-15-6/Succinic Acid; 110-16-7/maleic acid; 110-17-8/fumaric acid; 580-72-3/matairesinol; 7440-18-8/Ruthenium; 7782-39-0/Deuterium; 96-48-0/4-Butyrolactone

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