1: 93 percent / KOH (50percent) / tetrabutylammonium iodide / H2O; CH2Cl2 2: FeCl3 3: NH3 / methanol 4: Dess Martin periodane 5: 85 percent 6: 70 percent / ruthenium carbene complex (5percent w/w) / toluene / 48 h / 110 °C 7: 1.) OsO4, N-methyl morfoline N-oxide; 2.) SOCl2 / 2.) TEA 8: NaIO4 / RuCl3 / H2O; acetonitrile; CH2Cl2 9: 1.) NaBH4; 2.) H2SO4 (20percent aq) / 1.) dimethyl acetamide; 2.) Et2O 10: BH3DMS, H2 / Pd/C View Scheme

hydrogenchloride; hydrogen; palladium dihydroxide; palladium on activated charcoal in methanol; ethanol 48 h;