Dowex 1(BH4-); Dowex 1(IO4-) 1) 80percent aq. MeOH, r.t., 1.5 h, 2) r.t., 1.5 h; Yield given. Multistep reaction;

methanol; Dowex 50(H+) 0.666667 h; Heating;

1: 93 percent 2: AcOH, conc. H2SO4 / CH2Cl2 / 16 h / 4 °C 3: 68.5 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 12 h / Heating 4: 63 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 1.5 h / 90 °C 5: (dimethylamino)pyridine / acetonitrile 6: 85 percent / tributyltin hydride, AIBN / toluene / 120 °C 7: 1.) LiN3, benzoic acid, 2.) 0.1 M NaOCH3 / 1.) DMF, 120 deg C, 12 h, 2.) MeOH View Scheme

1: (dimethylamino)pyridine / acetonitrile 2: 85 percent / tributyltin hydride, AIBN / toluene / 120 °C 3: 1.) LiN3, benzoic acid, 2.) 0.1 M NaOCH3 / 1.) DMF, 120 deg C, 12 h, 2.) MeOH View Scheme

1: AcOH, conc. H2SO4 / CH2Cl2 / 16 h / 4 °C 2: 68.5 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 12 h / Heating 3: 63 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 1.5 h / 90 °C 4: (dimethylamino)pyridine / acetonitrile 5: 85 percent / tributyltin hydride, AIBN / toluene / 120 °C 6: 1.) LiN3, benzoic acid, 2.) 0.1 M NaOCH3 / 1.) DMF, 120 deg C, 12 h, 2.) MeOH View Scheme

1: 85 percent / tributyltin hydride, AIBN / toluene / 120 °C 2: 1.) LiN3, benzoic acid, 2.) 0.1 M NaOCH3 / 1.) DMF, 120 deg C, 12 h, 2.) MeOH View Scheme

1: 63 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 1.5 h / 90 °C 2: (dimethylamino)pyridine / acetonitrile 3: 85 percent / tributyltin hydride, AIBN / toluene / 120 °C 4: 1.) LiN3, benzoic acid, 2.) 0.1 M NaOCH3 / 1.) DMF, 120 deg C, 12 h, 2.) MeOH View Scheme

1: 68.5 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 12 h / Heating 2: 63 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 1.5 h / 90 °C 3: (dimethylamino)pyridine / acetonitrile 4: 85 percent / tributyltin hydride, AIBN / toluene / 120 °C 5: 1.) LiN3, benzoic acid, 2.) 0.1 M NaOCH3 / 1.) DMF, 120 deg C, 12 h, 2.) MeOH View Scheme

1: conc. H2SO4 / acetone; dimethylformamide / 0.5 h 2: 91 percent / pyridine / 4 h / Ambient temperature 3: 82 percent / LiN3 / dimethylformamide / 5 h / 100 °C 4: 94 percent / Dowex 50(H+), 80percent aq. MeOH / 0.67 h / Heating View Scheme

1: 91 percent / pyridine / 4 h / Ambient temperature 2: 82 percent / LiN3 / dimethylformamide / 5 h / 100 °C 3: 94 percent / Dowex 50(H+), 80percent aq. MeOH / 0.67 h / Heating View Scheme