1: 1.06 g / diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C 2: 820 mg / N-methylmorpholine N-oxide / OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 24 h / 20 °C 3: H5IO6 / tetrahydrofuran; H2O / 3 h / 20 °C 4: 732 mg / methanol; benzene; hexane / 15 h / 20 °C 5: 91 percent / lithium; t-BuOH / liquid ammonia; tetrahydrofuran / 2 h / -78 °C 6: 90 percent / CrO3; pyridine / CH2Cl2 / 0.5 h / 20 °C 7: 82 percent / SmI2; methanol / tetrahydrofuran / 2 h 8: 24 percent / imidazole; DMAP / dimethylformamide / 22 h / 20 °C 9: 92 percent / N-methylmorpholine N-oxide / TPAP / CH2Cl2 / 0.5 h / 20 °C 10: 76 percent / NaOMe / methanol / 12 h / 20 °C 11: 99 percent / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C 12: 95 percent / TBAF / tetrahydrofuran / 3 h 13: 61 percent / p-toluenesulfonic acid / benzene / 48 h / 60 °C 14: 76 percent / CuBr2 / acetonitrile / 72 h / 50 °C 15: 71 percent / Li2CO3; LiBr / dimethylformamide / 17 h / 140 °C View Scheme