sodium chlorite; sodium dihydrogenphosphate in tetrahydrofuran; water; tert-butyl alcohol T=20°C; 0.5 h; Schlenk technique;

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate T=80°C; 2 h;

thionyl chloride in N-methyl-acetamide; tetrachloromethane

1: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 2: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 3: IBX / ethyl acetate / 2 h / 80 °C View Scheme

1: 81 percent / pyridine / 1 h / 80 °C 2: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 3: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 4: IBX / ethyl acetate / 2 h / 80 °C View Scheme

1: 81 percent / pyridine / 1 h / 80 °C 2: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 3: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 4: IBX / ethyl acetate / 2 h / 80 °C View Scheme

1: With 1H-imidazole; N-(trimethylsilyl)-imidazole in toluene T=55°C; McFadyen-Stevens Reaction; 2: With citric acid in methanol T=20°C; McFadyen-Stevens Reaction;

sodium periodate in methanol; water T=20°C; 8 h; Schlenk technique;

1: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 2: IBX / ethyl acetate / 2 h / 80 °C View Scheme

1.1: potassium hydroxide / ethanol / 12 h / 80 °C / |Schlenk technique; |Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / |Schlenk technique; |Inert atmosphere 2.2: 10 h / 0 - 20 °C / |Schlenk technique; |Inert atmosphere 3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 12 h / 20 °C / |Schlenk technique 4.1: sodium periodate / water; methanol / 8 h / 20 °C / |Schlenk technique View Scheme