Document Detail


A biomimetic approach to the synthesis of an antiviral marine steroidal orthoester.
MedLine Citation:
PMID:  11950327     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Orthoesterol B, a marine natural product exhibiting antiviral activities, contains a [3.2.1]-bicyclic orthobutyrate bridging the steroid side chain and ring D. A biosynthetic reaction was proposed by which rearrangement of an epoxy ester results in the formation of the orthoester moiety. Steroidal model compounds incorporating 16-butyroxy and 20,22-epoxy groups were synthesized from tigogenin and were shown to rearrange to orthoesters under mild acidic catalysis.
Authors:
José-Luis Giner; Juan A Faraldos
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Apr 
Date Detail:
Created Date:  2002-04-12     Completed Date:  2002-08-15     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2717-20     Citation Subset:  IM    
Affiliation:
Department of Chemistry, SUNY-ESF, Syracuse, NY 13210, USA. jlginer@syr.edu
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MeSH Terms
Descriptor/Qualifier:
Animals
Antiviral Agents / chemical synthesis*
Cholestanes / chemistry
Chromatography, Thin Layer
Coronavirus / drug effects
Cyclization
Epoxy Compounds / chemical synthesis
Leukemia Virus, Feline / drug effects
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Mimicry
Molecular Structure
Orthomyxoviridae / drug effects
Porifera / chemistry
Steroids / chemical synthesis*,  chemistry,  isolation & purification,  pharmacology
Chemical
Reg. No./Substance:
0/Antiviral Agents; 0/Cholestanes; 0/Epoxy Compounds; 0/Steroids; 0/orthoesterol B

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