1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating 9: 98 percent / aq. TFA / methanol / 1 h View Scheme

1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating View Scheme