1: With lithium bromide; copper(ll) bromide in acetonitrile T=20°C; Inert atmosphereReflux; 2: With hydrogenchloride in diethyl ether; water; acetonitrile

hydrazine hydrate; potassium hydroxide in diethylene glycol T=200°C; Wolff-Kishner reduction;

lithium carbonate; lithium bromide in N,N-dimethyl-formamide T=140°C; 16 h;

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

1: 99 percent / 4-methylmorpholine N-oxide / OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 2: 98 percent / lead tetraacetate / benzene / 2 h / 20 °C 3: 1.06 g / diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C 4: 820 mg / N-methylmorpholine N-oxide / OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 24 h / 20 °C 5: H5IO6 / tetrahydrofuran; H2O / 3 h / 20 °C 6: 732 mg / methanol; benzene; hexane / 15 h / 20 °C 7: 91 percent / lithium; t-BuOH / liquid ammonia; tetrahydrofuran / 2 h / -78 °C 8: 90 percent / CrO3; pyridine / CH2Cl2 / 0.5 h / 20 °C 9: 82 percent / SmI2; methanol / tetrahydrofuran / 2 h 10: 24 percent / imidazole; DMAP / dimethylformamide / 22 h / 20 °C 11: 92 percent / N-methylmorpholine N-oxide / TPAP / CH2Cl2 / 0.5 h / 20 °C 12: 76 percent / NaOMe / methanol / 12 h / 20 °C 13: 99 percent / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C 14: 95 percent / TBAF / tetrahydrofuran / 3 h 15: 61 percent / p-toluenesulfonic acid / benzene / 48 h / 60 °C 16: 76 percent / CuBr2 / acetonitrile / 72 h / 50 °C 17: 71 percent / Li2CO3; LiBr / dimethylformamide / 17 h / 140 °C View Scheme

1: 98 percent / lead tetraacetate / benzene / 2 h / 20 °C 2: 1.06 g / diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C 3: 820 mg / N-methylmorpholine N-oxide / OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 24 h / 20 °C 4: H5IO6 / tetrahydrofuran; H2O / 3 h / 20 °C 5: 732 mg / methanol; benzene; hexane / 15 h / 20 °C 6: 91 percent / lithium; t-BuOH / liquid ammonia; tetrahydrofuran / 2 h / -78 °C 7: 90 percent / CrO3; pyridine / CH2Cl2 / 0.5 h / 20 °C 8: 82 percent / SmI2; methanol / tetrahydrofuran / 2 h 9: 24 percent / imidazole; DMAP / dimethylformamide / 22 h / 20 °C 10: 92 percent / N-methylmorpholine N-oxide / TPAP / CH2Cl2 / 0.5 h / 20 °C 11: 76 percent / NaOMe / methanol / 12 h / 20 °C 12: 99 percent / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C 13: 95 percent / TBAF / tetrahydrofuran / 3 h 14: 61 percent / p-toluenesulfonic acid / benzene / 48 h / 60 °C 15: 76 percent / CuBr2 / acetonitrile / 72 h / 50 °C 16: 71 percent / Li2CO3; LiBr / dimethylformamide / 17 h / 140 °C View Scheme

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

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

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

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