Abstract
Just a spoonful of sugar! A new synthetic strategy involving the use of a deoxygenative olefination reaction as the key step was developed for the preparation of deoxy and iminosugars in their optically active form (see scheme). This strategy has been proven successful by the use of a pentose, hexose, heptose, and disaccharide as the starting materials. Furthermore, it was applied in a formal total synthesis of iminosugar (-)-1-deoxy-L-fuconojirimycin, which can inhibit α-L-fucosidase.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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1-Deoxynojirimycin / analogs & derivatives
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1-Deoxynojirimycin / chemical synthesis
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1-Deoxynojirimycin / chemistry
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1-Deoxynojirimycin / pharmacology
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Alkenes / chemistry*
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Benzene Derivatives / chemistry
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Carbohydrates
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Imino Sugars / chemical synthesis*
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Imino Sugars / chemistry
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Oxidation-Reduction
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Stereoisomerism
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Sugar Alcohols / chemical synthesis
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Sugar Alcohols / chemistry
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Sugar Alcohols / pharmacology
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alpha-L-Fucosidase / antagonists & inhibitors
Substances
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Alkenes
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Benzene Derivatives
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Carbohydrates
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Imino Sugars
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Sugar Alcohols
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benzyne
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1-Deoxynojirimycin
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deoxyfuconojirimycin
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alpha-L-Fucosidase