1: 62 percent / sodium hydride, tetrabutylammonium iodide / dimethylformamide / 48 h / 50 °C 2: 78 percent / 6N HCl/silica gel / CH2Cl2 / 2 h / 20 °C 3: 1.) n-butyllithium / 1.) THF, 20 deg C, 20 min, 2.) THF, 20 deg C, 4 h 4: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 3N NaOH, 30percent H2O2 / 1.) THF, 15 h, 2.) THF, ethanol 5: 70 percent / imidazole / dimethylformamide / 3 h / 0 °C 6: 70 percent / H2 / 20percent Pd/C / ethanol / 5 h / 2280 Torr 7: 81 percent / Jones reagent / acetone / 0 °C 8: 69 percent / 1percent HCl / methanol / 4 h / 20 °C View Scheme