1: 87 percent / diethyl ether; pyridine / 0 deg C, 2 h. then 22 deg C, 24 h. 2: 77 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 22 °C 3: N-methylmorpholine N-oxide hydrate, osmium tetroxide / H2O; 2-methyl-propan-2-ol; acetone / 24 h / 22 °C 4: 79 percent / hydrazine hydrate / ethanol / 2 h / 60 °C 5: 85 percent / aq. KOH / methanol / 22 deg C, 12 h. then 60 deg C, 3 h. View Scheme

With  perchloric acid in  1,4-dioxane 5 h;  Ambient temperature;   

Multi-step reaction with 2 steps 1: 87 percent / diethyl ether; pyridine / 0 deg C, 2 h. then 22 deg C, 24 h.2: 77 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 22 °C  

Multi-step reaction with 3 steps 1: 87 percent / diethyl ether; pyridine / 0 deg C, 2 h. then 22 deg C, 24 h.2: 77 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 22 °C3: N-methylmorpholine N-oxide hydrate, osmium tetroxide / H2O; 2-methyl-propan-2-ol; acetone / 24 h / 22 °C  

Multi-step reaction with 3 steps 1: 87 percent / diethyl ether; pyridine / 0 deg C, 2 h. then 22 deg C, 24 h.2: 77 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 22 °C3: 1.) N-methylmorpholine N-oxide hydrate, osmium tetroxide; 2.) conc. sulfuric acid / 1.) water, acetone, t-butanol, 22 deg C, 24 h.; 2.) 22 deg C, 48 h.  

Multi-step reaction with 4 steps 1: 87 percent / diethyl ether; pyridine / 0 deg C, 2 h. then 22 deg C, 24 h.2: 77 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 22 °C3: N-methylmorpholine N-oxide hydrate, osmium tetroxide / H2O; 2-methyl-propan-2-ol; acetone / 24 h / 22 °C4: 79 percent / hydrazine hydrate / ethanol / 2 h / 60 °C