tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 18 h; Inert atmosphere;

1: p-toluene sulfonic acid / 6 h / Ambient temperature 2: tetramethylguanidine 3: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1.) 18 h, RT 2.) 3 h, 60 deg C 4: 70 percent / NH4OAc, 15percent aq. TiCl3 / tetrahydrofuran / Ambient temperature 5: NaBH4 / methanol / 2 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in ethanol; acetic acid

1: 1.) NBS 2.) H2O / 2.) heated 2: 35 percent / methanol; pyridine / 0.33 h / Ambient temperature 3: 85 percent / AcONH4, 15percent aq. TiCl3 / tetrahydrofuran; H2O / 1 h / 60 °C 4: p-toluene sulfonic acid / 6 h / Ambient temperature 5: tetramethylguanidine 6: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1.) 18 h, RT 2.) 3 h, 60 deg C 7: 70 percent / NH4OAc, 15percent aq. TiCl3 / tetrahydrofuran / Ambient temperature 8: NaBH4 / methanol / 2 h / Ambient temperature View Scheme

1: 35 percent / methanol; pyridine / 0.33 h / Ambient temperature 2: 85 percent / AcONH4, 15percent aq. TiCl3 / tetrahydrofuran; H2O / 1 h / 60 °C 3: p-toluene sulfonic acid / 6 h / Ambient temperature 4: tetramethylguanidine 5: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1.) 18 h, RT 2.) 3 h, 60 deg C 6: 70 percent / NH4OAc, 15percent aq. TiCl3 / tetrahydrofuran / Ambient temperature 7: NaBH4 / methanol / 2 h / Ambient temperature View Scheme

1: p-toluene sulfonic acid / 6 h / Ambient temperature 2: tetramethylguanidine 3: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1.) 18 h, RT 2.) 3 h, 60 deg C 4: 70 percent / NH4OAc, 15percent aq. TiCl3 / tetrahydrofuran / Ambient temperature 5: NaBH4 / methanol / 2 h / Ambient temperature View Scheme

1: tetramethylguanidine 2: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1.) 18 h, RT 2.) 3 h, 60 deg C 3: 70 percent / NH4OAc, 15percent aq. TiCl3 / tetrahydrofuran / Ambient temperature 4: NaBH4 / methanol / 2 h / Ambient temperature View Scheme

1: 85 percent / AcONH4, 15percent aq. TiCl3 / tetrahydrofuran; H2O / 1 h / 60 °C 2: p-toluene sulfonic acid / 6 h / Ambient temperature 3: tetramethylguanidine 4: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1.) 18 h, RT 2.) 3 h, 60 deg C 5: 70 percent / NH4OAc, 15percent aq. TiCl3 / tetrahydrofuran / Ambient temperature 6: NaBH4 / methanol / 2 h / Ambient temperature View Scheme

1: p-TsOH / CH2Cl2 2: Bu3SnH, AIBN / benzene 3: H2 / 10 percent Pd/C / ethanol; acetic acid View Scheme

1: Bu3SnH, AIBN / benzene 2: H2 / 10 percent Pd/C / ethanol; acetic acid View Scheme