1: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 2: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 3: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 4: tetrazole / CH2Cl2 / 0 °C 5: t-BuOOH / CH2Cl2 / 0 °C 6: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 7: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: 98 percent / CeCl3 / tetrahydrofuran / -50 °C 2: 95 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 3: 63 percent / NaI; AcOH / 20 °C 4: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 5: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 6: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 7: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 8: tetrazole / CH2Cl2 / 0 °C 9: t-BuOOH / CH2Cl2 / 0 °C 10: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 11: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 2: 98 percent / CeCl3 / tetrahydrofuran / -50 °C 3: 95 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 4: 63 percent / NaI; AcOH / 20 °C 5: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 6: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 7: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 8: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 9: tetrazole / CH2Cl2 / 0 °C 10: t-BuOOH / CH2Cl2 / 0 °C 11: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 12: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: 63 percent / NaI; AcOH / 20 °C 2: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 3: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 4: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 5: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 6: tetrazole / CH2Cl2 / 0 °C 7: t-BuOOH / CH2Cl2 / 0 °C 8: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 9: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 2: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 3: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 4: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 5: tetrazole / CH2Cl2 / 0 °C 6: t-BuOOH / CH2Cl2 / 0 °C 7: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 8: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: 99 percent / DDQ; H2O / CH2Cl2 / 0 °C 2: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 3: 98 percent / CeCl3 / tetrahydrofuran / -50 °C 4: 95 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 5: 63 percent / NaI; AcOH / 20 °C 6: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 7: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 8: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 9: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 10: tetrazole / CH2Cl2 / 0 °C 11: t-BuOOH / CH2Cl2 / 0 °C 12: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 13: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 2: 79 percent / aq. HF; pyridine / acetonitrile View Scheme

1.1: TEA / CH2Cl2 / 3 h / 0 °C 2.1: 92 percent / K2CO3; MeSO4NH2; K2OsO2(OH)4 / (DHQD)2PHAL / 2-methyl-propan-2-ol / 2 h / 0 °C 3.1: p-TsOH / 1 h / 20 °C 4.1: Zn(NO3)2*6H2O / acetonitrile / 3 h / 50 °C 5.1: Bu2SnO / toluene / 12 h / Heating 5.2: 84 percent / Bu4NI / 1.5 h / Heating 6.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 87 percent / KOH / methanol; tetrahydrofuran / 1 h / 20 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 20 °C 9.1: DBU; LiCl / acetonitrile / 2.5 h / 20 °C 10.1: 85 percent / (R)-BINAl-H / tetrahydrofuran / 6 h / -100 °C 11.1: 92 percent / p-TsOH / benzene / 0.5 h / Heating 12.1: 94 percent / NaHMDS; TMSCl / tetrahydrofuran / 4 h / -78 °C 13.1: 94 percent / H2O2; NaHCO3 / ethyl acetate; tetrahydrofuran / 0.5 h / 20 °C 14.1: 96 percent / DDQ; water / CH2Cl2 / 0.5 h / 20 °C 15.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1 h / 20 °C 16.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -100 - 0 °C 17.1: 89 percent / HCl / methanol / 10 h / 20 °C 18.1: 2,6-lutidine / 0.17 h / -78 °C 19.1: -78 - 20 °C 20.1: 70 percent / HCl / tetrahydrofuran; acetonitrile / 2 h / -10 °C 21.1: 80 percent / PdCl2(MeCN)2 / dimethylformamide / 25 h / 20 °C 22.1: PCl3; pyridine 22.2: 56 percent / TBHP / CH2Cl2 23.1: HF / acetonitrile 23.2: 38 percent / pyridine / 20 h / 20 °C View Scheme

1.1: LiAlH4 / diethyl ether / 2.5 h / 0 - 20 °C 2.1: TEA / CH2Cl2 / 3 h / 0 °C 3.1: 92 percent / K2CO3; MeSO4NH2; K2OsO2(OH)4 / (DHQD)2PHAL / 2-methyl-propan-2-ol / 2 h / 0 °C 4.1: p-TsOH / 1 h / 20 °C 5.1: Zn(NO3)2*6H2O / acetonitrile / 3 h / 50 °C 6.1: Bu2SnO / toluene / 12 h / Heating 6.2: 84 percent / Bu4NI / 1.5 h / Heating 7.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 87 percent / KOH / methanol; tetrahydrofuran / 1 h / 20 °C 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 20 °C 10.1: DBU; LiCl / acetonitrile / 2.5 h / 20 °C 11.1: 85 percent / (R)-BINAl-H / tetrahydrofuran / 6 h / -100 °C 12.1: 92 percent / p-TsOH / benzene / 0.5 h / Heating 13.1: 94 percent / NaHMDS; TMSCl / tetrahydrofuran / 4 h / -78 °C 14.1: 94 percent / H2O2; NaHCO3 / ethyl acetate; tetrahydrofuran / 0.5 h / 20 °C 15.1: 96 percent / DDQ; water / CH2Cl2 / 0.5 h / 20 °C 16.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1 h / 20 °C 17.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -100 - 0 °C 18.1: 89 percent / HCl / methanol / 10 h / 20 °C 19.1: 2,6-lutidine / 0.17 h / -78 °C 20.1: -78 - 20 °C 21.1: 70 percent / HCl / tetrahydrofuran; acetonitrile / 2 h / -10 °C 22.1: 80 percent / PdCl2(MeCN)2 / dimethylformamide / 25 h / 20 °C 23.1: PCl3; pyridine 23.2: 56 percent / TBHP / CH2Cl2 24.1: HF / acetonitrile 24.2: 38 percent / pyridine / 20 h / 20 °C View Scheme

1.1: 92 percent / K2CO3; MeSO4NH2; K2OsO2(OH)4 / (DHQD)2PHAL / 2-methyl-propan-2-ol / 2 h / 0 °C 2.1: p-TsOH / 1 h / 20 °C 3.1: Zn(NO3)2*6H2O / acetonitrile / 3 h / 50 °C 4.1: Bu2SnO / toluene / 12 h / Heating 4.2: 84 percent / Bu4NI / 1.5 h / Heating 5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 6.1: 87 percent / KOH / methanol; tetrahydrofuran / 1 h / 20 °C 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 20 °C 8.1: DBU; LiCl / acetonitrile / 2.5 h / 20 °C 9.1: 85 percent / (R)-BINAl-H / tetrahydrofuran / 6 h / -100 °C 10.1: 92 percent / p-TsOH / benzene / 0.5 h / Heating 11.1: 94 percent / NaHMDS; TMSCl / tetrahydrofuran / 4 h / -78 °C 12.1: 94 percent / H2O2; NaHCO3 / ethyl acetate; tetrahydrofuran / 0.5 h / 20 °C 13.1: 96 percent / DDQ; water / CH2Cl2 / 0.5 h / 20 °C 14.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1 h / 20 °C 15.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -100 - 0 °C 16.1: 89 percent / HCl / methanol / 10 h / 20 °C 17.1: 2,6-lutidine / 0.17 h / -78 °C 18.1: -78 - 20 °C 19.1: 70 percent / HCl / tetrahydrofuran; acetonitrile / 2 h / -10 °C 20.1: 80 percent / PdCl2(MeCN)2 / dimethylformamide / 25 h / 20 °C 21.1: PCl3; pyridine 21.2: 56 percent / TBHP / CH2Cl2 22.1: HF / acetonitrile 22.2: 38 percent / pyridine / 20 h / 20 °C View Scheme