1.1: 92 percent / pyridine 2.1: AcOH; H2O / 3 h / 90 °C 2.2: 54 percent / pyridine / 12 h / 20 °C View Scheme

1: 90 percent / pyridine / 3 h / Ambient temperature 2: 80percent AcOH / 4 h / 90 °C 3: pyridine / 72 h / Ambient temperature 4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH3CN, room temperature, 1 h, 2.) 60 deg C, 2 h 5: 95 percent / NaOMe / methanol / 0.17 h / Ambient temperature 6: 1.) pTsCl, 2.) NaH / 1.) CH2Cl2, Py, -10 deg C, 3 h, 2.) DMF, 0 deg C, 12 h 7: 78 percent / H2 / Pd(OH)2/C / ethanol / 4 h View Scheme

1: 99 percent / pyridine 2: 95 percent / HCl, H2O 3: 97 percent / pyridine 4: 66 percent / Me3SiOTf / CH2Cl2 5: NH3 / methanol 6: NaH / dimethylformamide 7: 1.) HMDS, 2.) NBS, molecular sieves 4 Angstroem / 2.) CH2Cl2 8: 12 percent / H2 / Pd(OH)2/C / ethanol View Scheme