Synthesis of Kifunensine, an Immunomodulating Substance Isolated from a Microbial Source.

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Kifunensine (1), a novel immunomodulat isolated from an actinomycete, was enantiospecifically synthesized from D-mannosamine via a double cyclization of the oxamide-aldehyde precursor with ammonia as a key stop. The absolute stereochemistry of natural kifunensine was confirmed to be the D form.

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