1: 1) BuLi / 1) hexane, 2) THF, -78 deg C, 0.5 h 2: 92 percent / N-bromosuccinimide, H2O / tetrahydrofuran / 0.5 h / 0 °C 3: 89 percent / NaOAc, pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature 4: 97 percent / CeCl3, NaBH4 / methanol; CH2Cl2 / 0.17 h / 0 °C 5: 94 percent / toluene p-sulfonic acid / CH2Cl2 / 2 h / Ambient temperature 6: 1) CuI / 1) Et2O, 2) Et2O, -10 deg C, 1 h 7: 1) LAH, 2) 20percent aq. NaOH / 1) Et2O, r. t., 3 h, 2) r. t., 0 5 h 8: N(Et)3 / CH2Cl2 / 0.17 h / 0 °C 9: 1) LAH, 2) 20percent aq. NaOH / 1) Et2O, r. t., 3 h, 2) r. t., 0.5 h 10: 94 percent / 10percent HCl / tetrahydrofuran / 3 h / Heating View Scheme

tert.-butyl lithium in diethyl ether T=-78 - 20°C; Methylation;