Document Detail


Synthesis of γ- and δ-Lactone Natural Products by Employing a trans-cis Isomerization/Lactonization Strategy.
MedLine Citation:
PMID:  23546007     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford γ-lactone or δ-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy-2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5-hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)-parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.
Authors:
Machiko Ono; Keisuke Kato; Hiroyuki Akita
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  61     ISSN:  1347-5223     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2013  
Date Detail:
Created Date:  2013-04-02     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  464-70     Citation Subset:  IM    
Affiliation:
School of Pharmaceutical Sciences, International University of Health and Welfare.
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