1: 88 percent / Py 2: 87 percent / KI / acetone 3: 92 percent / dimethylformamide / 3 h / Heating 4: 81 percent / butyllithium / tetrahydrofuran; pentane / Ambient temperature 5: 74 percent / Li, NH3, ethanol / tetrahydrofuran / 0.5 h / -78 °C 6: 87 percent / glacial AcOH / 6 h / Ambient temperature 7: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 8: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme

Stage #1: With  sodium hydrogencarbonate; ozone in  tetrahydrofuran; methanol T=-78°C; 0.25 h; Stage #2: With  sodium tetrahydroborate in  tetrahydrofuran; methanol T=-78 - 20°C; 1 h;   

With  toluene-4-sulfonic acid in  1,4-dioxane; water T=80°C; 1 h;