1: 95 percent / pyridine / 23 h / 0 - 20 °C 2: 1.) n-BuLI, 2.) / 1.) dioxane, from 5 deg C to 25 deg C, 1.5 h, 2.) dioxane, reflux, 40 h 3: 99 percent / NaHCO3, H2 / 5percent Rh/C / ethyl acetate / 18 h / 760 Torr 4: 87 percent / AG 50W-X4 / CH2Cl2; methanol / 1 h / Ambient temperature 5: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 6: 98 percent / CH2Cl2 / 18 h / Ambient temperature 7: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

hydrogen fluoride in acetonitrile 1.5 h; Ambient temperature;

pyridine T=0 - 20°C; 23 h;