A novel carbocyclic ring closure of hex-5-enopyranosides and pent-4-enofuranosides

Nitrile oxide cycloadditions to hex-5-enopyranosides and pent-4-enofuranosides give spiroisoxazolines, which upon reductive opening of the heterocyclic ring undergo spontaneous intramolecular aldol-like condensation to give six- and five-membered densely functionalised carbocycles.

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Bibliographic Details
Published inSynlett no. 8; pp. 1289 - 1291
Main Authors Gallos, JK, Koftis, TV, Koumbis, AE, Moutsos
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
carbohydrates
ROUTE
carbocycles
CONVERSION
D-RIBOSE
SUGARS
hydrogenation
enaminones
REARRANGEMENT
FREE-RADICAL CYCLIZATIONS
CYCLOADDITION
CYCLOHEXANONES
nitrile oxides
CARBOHYDRATE-DERIVATIVES
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Summary:Nitrile oxide cycloadditions to hex-5-enopyranosides and pent-4-enofuranosides give spiroisoxazolines, which upon reductive opening of the heterocyclic ring undergo spontaneous intramolecular aldol-like condensation to give six- and five-membered densely functionalised carbocycles.
ISSN:0936-5214
DOI:10.1055/s-1999-2792