1: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating 2: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C 3: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 4: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h 5: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h 6: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C 7: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C 8: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C 9: 40 percent / t-BuOK / 2 h / 20 °C View Scheme