1: 91 percent / lithium; t-BuOH / liquid ammonia; tetrahydrofuran / 2 h / -78 °C 2: 90 percent / CrO3; pyridine / CH2Cl2 / 0.5 h / 20 °C 3: 82 percent / SmI2; methanol / tetrahydrofuran / 2 h 4: 24 percent / imidazole; DMAP / dimethylformamide / 22 h / 20 °C 5: 92 percent / N-methylmorpholine N-oxide / TPAP / CH2Cl2 / 0.5 h / 20 °C 6: 76 percent / NaOMe / methanol / 12 h / 20 °C 7: 99 percent / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C 8: 95 percent / TBAF / tetrahydrofuran / 3 h 9: 61 percent / p-toluenesulfonic acid / benzene / 48 h / 60 °C 10: 76 percent / CuBr2 / acetonitrile / 72 h / 50 °C 11: 71 percent / Li2CO3; LiBr / dimethylformamide / 17 h / 140 °C View Scheme