Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)-1,4-Dideoxymannojirimycin and Further Polyoxygenated 2-Pyperidones

摘要

abstract_textpThe total synthesis of (+)-1,4-dideoxymannojimycin and the enantiopure synthesis of three polyoxygenated piperidin-2-ones from a novel chiron is reported. Starting from 3-deoxy-3amine- D-glucose, by means of the stereoselective aqueous SHOWO protocol ( Sequential-Hydrolysis-Oxidation-Wittig Olefination), the unsaturated-7,3-lactam-D-xylofuranose derivative was prepared, which depending on the oxidative C - C bond cleavage reaction conditions for the furanose moiety, is transformed into either (+)-1,4-dideoxymannojirimycin or polyoxygenated piperidin-2-ones./p/abstract_text