Abstract
An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry*
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Alkaloids / pharmacology
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Glycoside Hydrolases / antagonists & inhibitors
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Glycoside Hydrolases / metabolism
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Molecular Structure
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Nitrogen Oxides / chemistry
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Tartrates / chemistry
Substances
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Alkaloids
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Enzyme Inhibitors
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Nitrogen Oxides
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Tartrates
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nitrones
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lentiginosine
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Glycoside Hydrolases
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tartaric acid