1: 52 percent / Zn(Hg), TMSCl / tetrahydrofuran / 12 h / Ambient temperature 2: 93 percent / OsO4, NMMNO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 22 h / Ambient temperature View Scheme

Zn–Hg amalgam; osmium(VIII) oxide; chloro-trimethyl-silane; CF3CO3H; 4-methylmorpholine N-oxide 1.) THF, rt., 12 h; 2.) THF, aq. t-BuOH; 3.) CH2Cl2; Yield given. Multistep reaction;

Multi-step reaction with 7 steps 1: 72 percent / tetrahydrofuran / 24 h / Ambient temperature2: 86 percent / 1.) H2O2, 4 M NaOH; 2.) Ac2O, pyridine / ethanol / 1.) 35 deg C, 4 h3: 1.) NaH; 2.) Ac2O, pyridine / 1.) THF, rt., 2 h4: 30percent HClO4 / methanol / 0.17 h / Ambient temperature5: pyridinium dichromate / CH2Cl2 / 5 h / Ambient temperature6: hydrogen / PtO2 / ethanol; ethyl acetate / Ambient temperature7: 1.) LiAlH4; 2.) pTsOH; 3.) CrO3, pyridine; 4.) tris-(triphenylphosphine) rhodium chloride; 5.) 5percent HCl / 1.) THF, rt., 4 h; 2.) 2,2-dimethoxypropane; 4.) toluene, reflux; 5.) MeOH  

Multi-step reaction with 2 steps 1: hydrogen / PtO2 / ethanol; ethyl acetate / Ambient temperature2: 1.) LiAlH4; 2.) pTsOH; 3.) CrO3, pyridine; 4.) tris-(triphenylphosphine) rhodium chloride; 5.) 5percent HCl / 1.) THF, rt., 4 h; 2.) 2,2-dimethoxypropane; 4.) toluene, reflux; 5.) MeOH  

With  pyridine; chromium(VI) oxide; hydrogenchloride; Wilkinson's catalyst; lithium aluminium tetrahydride; toluene-4-sulfonic acid  1.) THF, rt., 4 h; 2.) 2,2-dimethoxypropane; 4.) toluene, reflux; 5.) MeOH;  Yield given. Multistep reaction;