sodium acetate; toluene-4-sulfonic acid hydrazide in ethylene glycol dimethyl ether; water 6 h; Radiolysis;

1: AD-mix-β, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 2: 1.) aq. KOH, 2.) aq. HCl / 1.) MeOH 3: TsOH / CH2Cl2 / 1 h / Ambient temperature 4: imidazole / dimethylformamide / 16 h / Ambient temperature 5: H2 / Pd/C (10percent) / methanol; propionic acid / 24 h 6: PCC, celite / CH2Cl2 / 2 h 7: 1.) KN(SiMe3)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h 8: Bu4NF / dimethylformamide / 2 h / Ambient temperature 9: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 10: PPH3, DEAD / benzene / 16 h 12: CH2Cl2 / 1 h / -20 - 0 °C 13: TsOH / methanol; H2O / 16 h / Ambient temperature 14: pyridine / 2 h / 100 °C 15: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 17: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 18: NaHCO3 / acetonitrile / 24 h / 45 °C 19: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 20: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 21: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: imidazole / dimethylformamide / 16 h / Ambient temperature 2: H2 / Pd/C (10percent) / methanol; propionic acid / 24 h 3: PCC, celite / CH2Cl2 / 2 h 4: 1.) KN(SiMe3)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h 5: Bu4NF / dimethylformamide / 2 h / Ambient temperature 6: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 7: PPH3, DEAD / benzene / 16 h 9: CH2Cl2 / 1 h / -20 - 0 °C 10: TsOH / methanol; H2O / 16 h / Ambient temperature 11: pyridine / 2 h / 100 °C 12: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 14: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 15: NaHCO3 / acetonitrile / 24 h / 45 °C 16: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 17: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 18: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: H2 / Pd/C (10percent) / methanol; propionic acid / 24 h 2: PCC, celite / CH2Cl2 / 2 h 3: 1.) KN(SiMe3)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h 4: Bu4NF / dimethylformamide / 2 h / Ambient temperature 5: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 6: PPH3, DEAD / benzene / 16 h 8: CH2Cl2 / 1 h / -20 - 0 °C 9: TsOH / methanol; H2O / 16 h / Ambient temperature 10: pyridine / 2 h / 100 °C 11: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 13: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 14: NaHCO3 / acetonitrile / 24 h / 45 °C 15: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 16: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 17: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: AD-mix-β, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 2: 1.) aq. KOH, 2.) aq. HCl / 1.) MeOH 3: TsOH / CH2Cl2 / 1 h / Ambient temperature 4: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 5: TsOH / benzene / 24 h / Heating 6: I2, PPh3, imidazole / toluene / 3 h / Ambient temperature 7: NaHCO3 / acetonitrile / 4 h / Heating 8: 1.) KN(SiMe3)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h 9: Bu4NF / dimethylformamide / 2 h / Ambient temperature 10: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 11: PPH3, DEAD / benzene / 16 h 13: CH2Cl2 / 1 h / -20 - 0 °C 14: TsOH / methanol; H2O / 16 h / Ambient temperature 15: pyridine / 2 h / 100 °C 16: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 18: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 19: NaHCO3 / acetonitrile / 24 h / 45 °C 20: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 21: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 22: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 2: TsOH / benzene / 24 h / Heating 3: I2, PPh3, imidazole / toluene / 3 h / Ambient temperature 4: NaHCO3 / acetonitrile / 4 h / Heating 5: 1.) KN(SiMe3)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h 6: Bu4NF / dimethylformamide / 2 h / Ambient temperature 7: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 8: PPH3, DEAD / benzene / 16 h 10: CH2Cl2 / 1 h / -20 - 0 °C 11: TsOH / methanol; H2O / 16 h / Ambient temperature 12: pyridine / 2 h / 100 °C 13: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 15: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 16: NaHCO3 / acetonitrile / 24 h / 45 °C 17: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 18: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 19: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 2: PPH3, DEAD / benzene / 16 h 4: CH2Cl2 / 1 h / -20 - 0 °C 5: TsOH / methanol; H2O / 16 h / Ambient temperature 6: pyridine / 2 h / 100 °C 7: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 9: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 10: NaHCO3 / acetonitrile / 24 h / 45 °C 11: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 12: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 13: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: PPH3, DEAD / benzene / 16 h 3: CH2Cl2 / 1 h / -20 - 0 °C 4: TsOH / methanol; H2O / 16 h / Ambient temperature 5: pyridine / 2 h / 100 °C 6: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 8: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 9: NaHCO3 / acetonitrile / 24 h / 45 °C 10: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 11: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 12: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

2: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 3: NaHCO3 / acetonitrile / 24 h / 45 °C 4: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 5: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 6: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme

1: TsOH / benzene / 24 h / Heating 2: I2, PPh3, imidazole / toluene / 3 h / Ambient temperature 3: NaHCO3 / acetonitrile / 4 h / Heating 4: 1.) KN(SiMe3)2 / 1.) -78 deg C, 2 h, 2.) THF-HMPA, -78 deg C -> r.t., 16 h 5: Bu4NF / dimethylformamide / 2 h / Ambient temperature 6: 1.) Re2O7, lutidine, 2.) TsOH / 1.) CH2Cl2, 4 h, 2.) dimethoxypropane, acetone, 1 h 7: PPH3, DEAD / benzene / 16 h 9: CH2Cl2 / 1 h / -20 - 0 °C 10: TsOH / methanol; H2O / 16 h / Ambient temperature 11: pyridine / 2 h / 100 °C 12: LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Heating 14: I2, PPh3, imidazole / CH2Cl2 / 1 h / Ambient temperature 15: NaHCO3 / acetonitrile / 24 h / 45 °C 16: 1.) n-BuLi / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C -> room temp., 1 h 17: H2, Rh(PPh3)3Cl / benzene; ethanol / 2 h / Ambient temperature 18: acetyl chloride / methanol; diethyl ether / 6 h / Heating View Scheme