1.1: lithium hydroxide hydrate / tetrahydrofuran; water / 12 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / |Cooling with ice 2.2: 2 h / 20 °C View Scheme

1.1: lithium hydroxide hydrate / tetrahydrofuran; water / 12 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / |Cooling with ice 2.2: 2 h / 20 °C View Scheme

1: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, from 0 deg C to RT, 3 h 2: 99 percent / 2N aq. HCl / methanol / 3 h / Heating 3: imidazole / tetrahydrofuran / 1.5 h / 0 - 20 °C 4: TEA, DMAP / CH2Cl2 / 0.17 h / 0 °C 5: 1.) PdCl2(CH3CN)2, 2.) n-Bu4NF, 3.) aq. K2CO3 6: TEA, DMAP / CH2Cl2 / Ambient temperature 7: PdCl2(CH3CN)2 / CH2Cl2 / 2 h / Ambient temperature 8: 1.) O3, 2.) Me2S / 1.) MeOH. -78 deg C, 2.) MeOH, RT, 5 h 9: NaBH4 / methanol / 3 h / Ambient temperature 10: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 11: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

1: 99 percent / 2N aq. HCl / methanol / 3 h / Heating 2: imidazole / tetrahydrofuran / 1.5 h / 0 - 20 °C 3: TEA, DMAP / CH2Cl2 / 0.17 h / 0 °C 4: 1.) PdCl2(CH3CN)2, 2.) n-Bu4NF, 3.) aq. K2CO3 5: TEA, DMAP / CH2Cl2 / Ambient temperature 6: PdCl2(CH3CN)2 / CH2Cl2 / 2 h / Ambient temperature 7: 1.) O3, 2.) Me2S / 1.) MeOH. -78 deg C, 2.) MeOH, RT, 5 h 8: NaBH4 / methanol / 3 h / Ambient temperature 9: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 10: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

1: imidazole / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: TEA, DMAP / CH2Cl2 / 0.17 h / 0 °C 3: 1.) PdCl2(CH3CN)2, 2.) n-Bu4NF, 3.) aq. K2CO3 4: TEA, DMAP / CH2Cl2 / Ambient temperature 5: PdCl2(CH3CN)2 / CH2Cl2 / 2 h / Ambient temperature 6: 1.) O3, 2.) Me2S / 1.) MeOH. -78 deg C, 2.) MeOH, RT, 5 h 7: NaBH4 / methanol / 3 h / Ambient temperature 8: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 9: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

1: PdCl2(CH3CN)2 / CH2Cl2 / 2 h / Ambient temperature 2: 1.) O3, 2.) Me2S / 1.) MeOH. -78 deg C, 2.) MeOH, RT, 5 h 3: NaBH4 / methanol / 3 h / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 5: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

1: NaBH4 / methanol / 3 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 3: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

1: 1.) PdCl2(CH3CN)2, 2.) n-Bu4NF, 3.) aq. K2CO3 2: TEA, DMAP / CH2Cl2 / Ambient temperature 3: PdCl2(CH3CN)2 / CH2Cl2 / 2 h / Ambient temperature 4: 1.) O3, 2.) Me2S / 1.) MeOH. -78 deg C, 2.) MeOH, RT, 5 h 5: NaBH4 / methanol / 3 h / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 2 h / -50 °C 7: p-TsOH / acetone / 10 h / Ambient temperature View Scheme

tin(ll) chloride 21 h; Heating;

1: NaBH4 / 0 - 10 °C 2: benzyltriethylammonium chloride View Scheme