Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

• Emine Salamci and
• Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

• stereospecifically new chlorocyclooctanetriols. Keywords: aminocyclitols; aminocyclooctanetriol; chlorocyclooctanetriol; cyclic sulfate; cyclitols; Introduction The synthesis of aminocyclitols has attracted attention because they contain substructures of many biologically active natural products [1][2][3]. They

• synthesis of chlorocyclooctanetriol 19 starting from the trans-epoxide 13 (Scheme 4). The hydroxy groups in 19 were acetylated to give 20 for further characterization of the structure. The position of the chlorine atom in 20 was confirmed with the help of the COSY spectra. The resonance signal of H-3

• method for the synthesis of a novel chlorocyclooctanetriol isomer, epoxy-diol 22, which was synthesized in our previous work [31], was hydrolysed by HCl(g) in MeOH, resulting in the formation of two chlorocyclooctanetriol isomers 23 and 24 in an 85:15 ratio (1H NMR) in 96% combined yield (Scheme 5