Abstract
The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 2,6-dihydroxyhastanecine via reaction sequence involving reduction of the lactone moiety, glycolic cleavage of the terminal diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbohydrates / chemistry
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Catalysis
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Chemistry / methods
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Crystallography, X-Ray / methods
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Hydrogen / chemistry
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Lactones / chemistry*
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Models, Chemical
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Molecular Conformation
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Molecular Structure
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Nitrogen Oxides / chemistry*
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Pyrrolizidine Alkaloids / chemical synthesis*
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Pyrrolizidine Alkaloids / chemistry
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Temperature
Substances
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Carbohydrates
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Lactones
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Nitrogen Oxides
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Pyrrolizidine Alkaloids
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nitrones
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Hydrogen