in decalin T=190 - 200°C; 2 h;

pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid in dimethyl sulfoxide; benzene T=50°C; 0.5 h;

sodium periodate in tetrahydrofuran 4.5 h; Ambient temperature;

sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide 1) acetone, H2O 2) THF, H2O; Yield given. Multistep reaction;

1: 1.) aq. HCl, NaNO2, 2.) aq. NaN3 / 1.) 0 deg C, 15 min, 2.) 0 deg C, 30 min 2: 89 percent / aq. OsO4, N-methylmorpholine N-oxide / acetone / 17 h / Ambient temperature 3: 70 percent / aq. NaIO4 / tetrahydrofuran / 4.5 h / Ambient temperature View Scheme

1: 1.) aq. HCl, NaNO2, 2.) NaN3 2: 50 percent / Pyridine, CF3COOH, Dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 0.5 h / 50 °C View Scheme