2: 95 percent / sodium bismethoxyethoxyaluminum hydride (Red-Al) / diethyl ether / 1.) 0 deg C, 1 h; 2.) room temp., 12 h 3: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 0 °C View Scheme

1: 14 percent / DMSO, NaHCO3 / 0.25 h / 150 °C 2: 81 percent / pyridinium chlorochromate / CH2Cl2 / Ambient temperature 3: 100 percent / 4 Angstroem molecular sieves / benzene / 3 h / Heating 4: 74 percent / tetrahydrofuran / -110 to -80 deg C 5: NaIO4 / methanol; H2O; tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 95 percent / py*TosOH / CH2Cl2 / 3 h / Ambient temperature 2: 14 percent / DMSO, NaHCO3 / 0.25 h / 150 °C 3: 81 percent / pyridinium chlorochromate / CH2Cl2 / Ambient temperature 4: 100 percent / 4 Angstroem molecular sieves / benzene / 3 h / Heating 5: 74 percent / tetrahydrofuran / -110 to -80 deg C 6: NaIO4 / methanol; H2O; tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 81 percent / pyridinium chlorochromate / CH2Cl2 / Ambient temperature 2: 100 percent / 4 Angstroem molecular sieves / benzene / 3 h / Heating 3: 74 percent / tetrahydrofuran / -110 to -80 deg C 4: NaIO4 / methanol; H2O; tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 100 percent / 4 Angstroem molecular sieves / benzene / 3 h / Heating 2: 74 percent / tetrahydrofuran / -110 to -80 deg C 3: NaIO4 / methanol; H2O; tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 74 percent / tetrahydrofuran / -110 to -80 deg C 2: NaIO4 / methanol; H2O; tetrahydrofuran / 3 h / Ambient temperature View Scheme

sodium periodate in tetrahydrofuran; methanol; water 3 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

45 h; Heating;

1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min; 2.) from -78 deg C to r.t. 2: 85 percent / CSA / methanol / 16 h / Ambient temperature 3: 64 percent / pyridine*SO3, Et3N / dimethylsulfoxide / 0.17 h View Scheme

1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min; 2.) from -78 deg C to r.t. 2: 85 percent / CSA / methanol / 16 h / Ambient temperature View Scheme