1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 5: 98 percent / DBU / xylene / 16.5 h / Heating 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme

1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 2: 100 percent / 4-DMAP, pyridine / 36 h 3: 98 percent / NaBH4 / methanol / 2.5 h 4: 94 percent / DIEA / CH2Cl2 / 6 h 5: 100 percent / TBAF / tetrahydrofuran / 24 h 6: 69 percent / 4-DMAP / acetonitrile / 11.5 h 7: 0.25 h / 24 - 200 °C / 12 Torr 8: DIEA / methanol / 2 h 9: 93 percent / 2 N aq. HCl / methanol / 23 h / Heating 10: 100 percent / DIEA / methanol / 4 h View Scheme

1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 5: 98 percent / DBU / xylene / 16.5 h / Heating 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C 7: DMAP, pyridine / 22 h View Scheme