Stereodivergent synthesis of new amino sugars, furanodictines A and B, starting from d-glucuronolactone

An efficient and divergent strategy for the total synthesis of the first 3,6-dihydroaminosugars, furanodictines A (2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-d-glucofuranose) and B (2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-d-mannofuranose), has been developed. The synthetic process is featured by readily accessible and stereodefined manipulation of highly functionalized bicyclic tetrahydrofuran derivatives incorporating the glucuronolactone (common starting material)-derived skeleton.