ammonia in methanol T=0 - 4°C; 48 h;

ammonia in ethanol T=0 - 20°C; 48 h;

ammonia in methanol T=20°C; 48 h;

Dowex(H+) in water

tetrabutyl ammonium fluoride in tetrahydrofuran

1: 1.) dibutylstannoxane; 2.) triethylamine / 1.) methanol, reflux, 1 h; 2.) methanol, 20 deg C, 2 h 2: 1.) CF3COOH; 2.) NaIO4; 3.) MeONa 3: 82 percent / 20 percent Pd(OH)2/C / ethanol; cyclohexene / 2.5 h / Heating 4: 90 percent / 4-dimethylaminopyridine / pyridine / 16 h / 20 °C 5: 1.) hexamethyldisilazane; 2.) CF3SO2SiMe3 / 1.) pyridine, reflux, 4 h; 2.) 1,2-dichloroethane, 20 deg C, 16 h 6: 72 percent / ammonia / methanol / 48 h / 20 °C View Scheme

1: 1.) CF3COOH; 2.) NaIO4; 3.) MeONa 2: 82 percent / 20 percent Pd(OH)2/C / ethanol; cyclohexene / 2.5 h / Heating 3: 90 percent / 4-dimethylaminopyridine / pyridine / 16 h / 20 °C 4: 1.) hexamethyldisilazane; 2.) CF3SO2SiMe3 / 1.) pyridine, reflux, 4 h; 2.) 1,2-dichloroethane, 20 deg C, 16 h 5: 72 percent / ammonia / methanol / 48 h / 20 °C View Scheme

1: 82 percent / 20 percent Pd(OH)2/C / ethanol; cyclohexene / 2.5 h / Heating 2: 90 percent / 4-dimethylaminopyridine / pyridine / 16 h / 20 °C 3: 1.) hexamethyldisilazane; 2.) CF3SO2SiMe3 / 1.) pyridine, reflux, 4 h; 2.) 1,2-dichloroethane, 20 deg C, 16 h 4: 72 percent / ammonia / methanol / 48 h / 20 °C View Scheme

1: OsO4; N-methylmorpholine-N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 120 h / 4 °C 2: pyridine 3: 93 percent / NaBH4 / dimethylformamide / 2 h / 20 °C 4: Bu4NF / tetrahydrofuran / 0.08 h / 20 °C View Scheme

1: pyridine 2: 93 percent / NaBH4 / dimethylformamide / 2 h / 20 °C 3: Bu4NF / tetrahydrofuran / 0.08 h / 20 °C View Scheme