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A simple method was developed for the direct formation of unsaturated iminosugars starting from readily available [omega]-methanesulfonylglycononitriles. The nucleophilic addition/cyclization reaction with variation of the Grignard reagent allows for a range of different side chains to be incorporated to generate libraries of broussonetine analogues.

An unprecedented reactivity of CF3-TMS has been revealed, which exploits the basic character of the generated [CF3-] capable of delivering dichloromethide from dichloromethane with subsequent transfer to nitrones under smooth conditions. The proton-abstraction pathway was demonstrated through isotopic labeling experiments in CD2Cl2. The same reaction was achieved in acetonitrile with the introduction of a cyanomethyl group onto the nitrones. [ABSTRACT FROM AUTHOR]

Polyhydroxylated quinolizidines bearing a hydroxymethyl group at the ring junction were synthesized from a readily available l-sorbose-derived ketonitrone. Evaluated as glycoside hydrolase inhibitors, these quinolizidines revealed to be potent and selective α-glucosidase inhibitors. Quinolizidine 9a is the first quinolizidine-scaffolded iminosugar exhibiting nanomolar inhibition of a glycoenzyme.

An unprecedented reactivity of CF3-TMS has been revealed, which exploits the basic character of the generated [CF3(-)] capable of delivering dichloromethide from dichloromethane with subsequent transfer to nitrones under smooth conditions. The proton-abstraction pathway was demonstrated through isotopic labeling experiments in CD2Cl2. The same reaction was achieved in acetonitrile with the introduction of a cyanomethyl group onto the nitrones.