Synthesims of 7-oxabicyclo[2.2.1]heptanes and 8-oxabicyclo[3.2.1]octanes from C-glycosides via an intramolecular cyclization

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DOIResolve DOI: http://doi.org/10.1021/jo3024973
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TypeArticle
Journal titleJournal of Organic Chemistry
ISSN0022-3263
Volume78
Issue6
Pages27032709; # of pages: 7
SubjectAnomeric configuration; C-glycosides; Chemical yields; Enamine intermediates; Epimerization; Intramolecular cyclizations; Nucleophilic substitutions; Pyrrolidines; Cyclization; Heptane; Stereoselectivity; Sugars; 7 oxabicyclo [2 2 1] heptane; 8 oxabicyclo [3 2 1]octane; glycoside; heptane; octane; pyrrolidine derivative; unclassified drug; bicyclo compound; C glycoside; C-glycoside; cycloheptane derivative; cyclooctane derivative; monosaccharide; article; chemical reaction; chemical structure; cyclization; epimerization; nucleophilicity; stereochemistry; synthesis; chemistry; cyclization; stereoisomerism; Bicyclo Compounds; Cyclization; Cycloheptanes; Cyclooctanes; Molecular Structure; Monosaccharides; Stereoisomerism
AbstractA simple and effective method for the synthesis of 7-oxabicyclo[2.2.1] heptanes and 8-oxabicyclo[3.2.1]octanes from acetonyl C-glycoside substrates is described, which involves an intramolecular cyclization reaction through a nucleophilic substitution at C-5 or C-6 of C-glycosides by a 2′-enamine intermediate formed in the presence of pyrrolidine. Because anomeric epimerization occurs under these conditions, C-glycoside substrates with either anomeric configuration were converted to the same product(s) in same stereoselectivity and similar chemical yield. © 2013 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Biological Sciences (IBS-ISB)
Peer reviewedYes
NPARC number21269925
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Record identifier8859ff11-0861-49b5-82f3-ed151ee60d6d
Record created2013-12-13
Record modified2016-05-09
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