1: 82 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -78 °C 2: 97 percent / potassium carbonate / acetonitrile / 5 h / Heating 3: 100 percent / tetra-n-butylammonium fluoride dihydrate / tetrahydrofuran / 14 h / 20 °C 4: (COCl)2; triethylamine / dimethylsulfoxide; CH2Cl2 / -78 - 20 °C 5: 71 percent / TiCl4 / CH2Cl2 / 15 h / -78 °C 6: OsO4; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 7: 45 mg / NaHCO3; NaIO4 / tetrahydrofuran; H2O / 3 h / 20 °C 8: 81 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 24 h / 20 °C View Scheme

hydrogenchloride in methanol; water T=70°C; 4 h;

hydrogenchloride in methanol; water T=70°C; 4 h;