1: With osmium(VIII) oxide; 4-methylmorpholine N-oxide in 1,4-dioxane T=20°C; 2: With sodium periodate in 1,4-dioxane T=20°C; 2 h;

1: formic acid / ethanol / 1 h / 20 °C 2: aq. oxalic acid / 1 h / 20 °C View Scheme

1: formic acid / ethanol / 1 h / 20 °C 2: aq. oxalic acid / 1 h / 20 °C View Scheme

1.1: nBuLi / tetrahydrofuran; hexane / 0.25 h / -70 - -50 °C 1.2: 97 percent / tetrahydrofuran; hexane / 2 h / Heating 2.1: 4-methylmorpholine N-oxide; aq. OsO4 / dioxane / 20 °C 2.2: sodium periodate / dioxane / 2 h / 20 °C View Scheme

1.1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C 2.1: thionyl chloride / dichloromethane / 3 h / 0 °C / |Reflux 3.1: sodium hydride / tetrahydrofuran 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 4.2: 2 h / 80 °C 5.1: ozone; dimethylsulfide / dichloromethane / 1 h / -78 - 20 °C View Scheme

1.1: thionyl chloride / dichloromethane / 3 h / 0 °C / |Reflux 2.1: sodium hydride / tetrahydrofuran 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 3.2: 2 h / 80 °C 4.1: ozone; dimethylsulfide / dichloromethane / 1 h / -78 - 20 °C View Scheme

1.1: sodium hydride / tetrahydrofuran 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: 2 h / 80 °C 3.1: ozone; dimethylsulfide / dichloromethane / 1 h / -78 - 20 °C View Scheme

1: 4 Angstroem molecular sieves / benzene 2: formic acid / ethanol / 0.17 h / Ambient temperature 3: 1 N aq. oxalic acid / CH2Cl2; diethyl ether / 0.5 h / Ambient temperature View Scheme

(i) EtOH, (ii) aq. HCl, acetone; Multistep reaction;