1: 1.) α-acetoxyisobutyryl bromide; 2.) Dowex 1x2 (OH-) resin / 1.) MeCN/H2O, RT, 1 h; 2.) MeOH, RT, 15 min 2: 87 percent / pyridine / 16 h / Ambient temperature 3: 90 percent / Et3N, (CH3)2BBr / CH2Cl2 / 0.25 h / -78 °C 4: 93 percent / Et3N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature 5: 10 percent / NaH / dimethylformamide / 1.) -5 to 0 deg C, 1 h; 2.) RT, 30 min 6: 69 percent / H2 / 5 percent Pd/C / aq. ethanol / 96 h / 760 Torr View Scheme

1: 89 percent / pyridine / 19 h / Ambient temperature 2: 93 percent / Et3N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature 3: 10 percent / NaH / dimethylformamide / 1.) -5 to 0 deg C, 1 h; 2.) RT, 30 min 4: 69 percent / H2 / 5 percent Pd/C / aq. ethanol / 96 h / 760 Torr View Scheme

1: 83 percent / SOCl2; pyridine / acetonitrile 2: 94 percent / Et3N / tetrahydrofuran; acetonitrile / 20 °C 3: 60 percent / KHCO3 / dimethylformamide / 264 h 4: 80 percent / NaOH / H2O; tetrahydrofuran 5: 90 percent / H2 / Pd(OH)2/C View Scheme

1: 94 percent / Et3N / tetrahydrofuran; acetonitrile / 20 °C 2: 60 percent / KHCO3 / dimethylformamide / 264 h 3: 80 percent / NaOH / H2O; tetrahydrofuran 4: 90 percent / H2 / Pd(OH)2/C View Scheme

1: 60 percent / KHCO3 / dimethylformamide / 264 h 2: 80 percent / NaOH / H2O; tetrahydrofuran 3: 90 percent / H2 / Pd(OH)2/C View Scheme

1: 70 percent / H2SO4 / 3 h / Ambient temperature 2: 60 percent / imidazole / pentane / 3 h / Ambient temperature 3: pyridine / CH2Cl2 / 0.25 h / -10 °C 4: 56 percent / NaN3 / pyridine / 120 h / Ambient temperature 5: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 6: 88 percent / pyridine / 5 h / Ambient temperature 7: 1,) conc. H2SO4, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight 8: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight 9: 52 percent / NH3 / tetrahydrofuran / 60 °C 10: 97 percent / H2 / Pd/C / ethanol / 6 h / 760 Torr View Scheme

1: 88 percent / pyridine / 5 h / Ambient temperature 2: 1,) conc. H2SO4, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight 3: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight 4: 52 percent / NH3 / tetrahydrofuran / 60 °C 5: 97 percent / H2 / Pd/C / ethanol / 6 h / 760 Torr View Scheme

1: 60 percent / imidazole / pentane / 3 h / Ambient temperature 2: pyridine / CH2Cl2 / 0.25 h / -10 °C 3: 56 percent / NaN3 / pyridine / 120 h / Ambient temperature 4: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 5: 88 percent / pyridine / 5 h / Ambient temperature 6: 1,) conc. H2SO4, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight 7: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight 8: 52 percent / NH3 / tetrahydrofuran / 60 °C 9: 97 percent / H2 / Pd/C / ethanol / 6 h / 760 Torr View Scheme

1: pyridine / CH2Cl2 / 0.25 h / -10 °C 2: 56 percent / NaN3 / pyridine / 120 h / Ambient temperature 3: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 4: 88 percent / pyridine / 5 h / Ambient temperature 5: 1,) conc. H2SO4, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight 6: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight 7: 52 percent / NH3 / tetrahydrofuran / 60 °C 8: 97 percent / H2 / Pd/C / ethanol / 6 h / 760 Torr View Scheme

1: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 2: 88 percent / pyridine / 5 h / Ambient temperature 3: 1,) conc. H2SO4, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight 4: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight 5: 52 percent / NH3 / tetrahydrofuran / 60 °C 6: 97 percent / H2 / Pd/C / ethanol / 6 h / 760 Torr View Scheme