1: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature 2: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature 3: 580 mg / pyridine / 16 h / Ambient temperature 4: NaBH4 / methanol; tetrahydrofuran / 3 h / Ambient temperature 5: 260 mg / pyridine / 3 h / Ambient temperature 6: 96 percent / NaI / acetone / 72 h / Heating 7: 98 percent / Bu3SnH / tetrahydrofuran / 18 h / Ambient temperature 8: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 9: pyridine / 2 h / Ambient temperature 10: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 11: 209 mg / LiBr / dimethylformamide / 1 h / Heating 12: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 13: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 2: pyridine / 2 h / Ambient temperature 3: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 4: 209 mg / LiBr / dimethylformamide / 1 h / Heating 5: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 6: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 2: 209 mg / LiBr / dimethylformamide / 1 h / Heating 3: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 4: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 209 mg / LiBr / dimethylformamide / 1 h / Heating 2: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 3: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

sodium hydroxide in methanol 3 h; Heating;

1: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 2: 80 percent / OsO4, K3<Fe(CN)6>, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme

1: 98 percent / propionic acid / xylene / 2 h / Heating 2: LiAlH4 / tetrahydrofuran / 2 h / Heating 3: Et3N / toluene / 2 h / 0 °C 4: LiAlH4 / tetrahydrofuran / Ambient temperature 5: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 6: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 7: 80 percent / OsO4, K3<Fe(CN)6>, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme

1: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 2: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 3: 80 percent / OsO4, K3<Fe(CN)6>, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme

1: LiAlH4 / tetrahydrofuran / 2 h / Heating 2: Et3N / toluene / 2 h / 0 °C 3: LiAlH4 / tetrahydrofuran / Ambient temperature 4: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 5: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 6: 80 percent / OsO4, K3<Fe(CN)6>, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme

1: LiAlH4 / tetrahydrofuran / Ambient temperature 2: 99 percent / 1 M H2SO4 / acetone / 2 h / Ambient temperature 3: 82 percent / pyridinium tolunen-p-sulfonate, LiBr / N,N-dimethyl-acetamide / 5 h / 160 °C 4: 80 percent / OsO4, K3<Fe(CN)6>, 1,4-bis(0-O-dihydroquinidinyl)phthalazine, K2CO3, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 15 h / Ambient temperature View Scheme