1: 88 percent / H2 / PtO2 / ethyl acetate; ethanol / 3 h / Ambient temperature 2: 96 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 3: p-TsOH / 0.33 h / Ambient temperature 4: CrO3, pyridine / 5 h / Ambient temperature 5: 2) 5percent HCl / 2) (PH3P)3RhCl / 1) toluene, 2h, reflux, 2) MeOH, overnight 6: 52 percent / Zn(Hg), TMSCl / tetrahydrofuran / 12 h / Ambient temperature 7: 93 percent / OsO4, NMMNO / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 22 h / Ambient temperature View Scheme

Multi-step reaction with 5 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 temperature  

Multi-step reaction with 2 steps 1: hydrogen / PtO2 / ethanol; ethyl acetate / Ambient temperature2: KBH4 / methanol; CH2Cl2  

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