Allylated monosaccharides as precursors in triple reductive amination strategies: synthesis of castanospermine and swainsonine.
The feasibility of the triple-reductive amination reaction for the synthesis of complex indolizidine frameworks is illustrated by application to the potent glycosidase inhibitors castanospermine and swainsonine. The target compounds were obtained from known carbohydrate precursors in yields of 23 and 14%, over nine and 13 steps, respectively. The iodoetherification reaction of allylated monosaccharides was shown to be a practical reaction for the synthesis of the tricarbonyl precursors for the key triple reductive amination reactions.
Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10021, USA.
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Zhao
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Cheng
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Mootoo
D000478:Alkylation; D000586:Amination; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines
D004791:Enzyme Inhibitors; D006026:Glycoside Hydrolases; D007212:Indolizines; D009005:Monosaccharides; D017026:Swainsonine; C037806:castanospermine; D054836:Indolizidines