title: Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid.
abstract: Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.
authors.affiliation: Department of Chemistry, Tamkang University, No151 Yingzhuan Rd, 25137 Tamsui Dist., New Taipei City, Taiwan. tlshih@mail.tku.edu.tw
authors.forename: Tzenge-Lien
authors.initials: TL
authors.lastname: Shih
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Yang
mesh_terms: D054812:Cyclitols / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D056004:Molecular Dynamics Simulation; D019906:Nuclear Magnetic Resonance, Biomolecular; D011801:Quinic Acid / Q000737:chemistry*; D019810:Sodium Azide / Q000737:chemistry
chemical_list: D054812:Cyclitols; D004852:Epoxy Compounds; D011801:Quinic Acid; D019810:Sodium Azide