hydrogen; palladium on activated charcoal in methanol; ethyl acetate

1: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 2: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme

1.1: 88 percent / LiOH*H2O; MS 4 Angstroem / tetrahydrofuran / 12 h / Heating 2.1: 90 percent / DIBAL-H / CH2Cl2 / 2 h / -78 - 20 °C 3.1: NaH / (nBu)4NI / tetrahydrofuran / 12 h / 20 °C 4.1: Et3Al; Fe(acac)3; DMO / toluene / 3 h / 55 °C 4.2: PPTS / CH2Cl2 / 12 h / 20 °C 5.1: O3; Ph3P / CH2Cl2 6.1: NaBH4 / methanol 7.1: AcOH / H2O / 75 °C 8.1: PCC / CH2Cl2 9.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 10.1: 85 percent / DDQ / CH2Cl2; H2O 11.1: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 12.1: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme

1: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 2: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme

1.1: 80 percent / CSA / 1,2-dichloro-ethane / Heating 2.1: TBAF / tetrahydrofuran 2.2: 87 percent / (COCl)2; Et3N; DMSO / CH2Cl2 3.1: 88 percent / LiOH*H2O; MS 4 Angstroem / tetrahydrofuran / 12 h / Heating 4.1: 90 percent / DIBAL-H / CH2Cl2 / 2 h / -78 - 20 °C 5.1: NaH / (nBu)4NI / tetrahydrofuran / 12 h / 20 °C 6.1: Et3Al; Fe(acac)3; DMO / toluene / 3 h / 55 °C 6.2: PPTS / CH2Cl2 / 12 h / 20 °C 7.1: O3; Ph3P / CH2Cl2 8.1: NaBH4 / methanol 9.1: AcOH / H2O / 75 °C 10.1: PCC / CH2Cl2 11.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 12.1: 85 percent / DDQ / CH2Cl2; H2O 13.1: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 14.1: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme

1.1: 90 percent / DIBAL-H / CH2Cl2 / 2 h / -78 - 20 °C 2.1: NaH / (nBu)4NI / tetrahydrofuran / 12 h / 20 °C 3.1: Et3Al; Fe(acac)3; DMO / toluene / 3 h / 55 °C 3.2: PPTS / CH2Cl2 / 12 h / 20 °C 4.1: O3; Ph3P / CH2Cl2 5.1: NaBH4 / methanol 6.1: AcOH / H2O / 75 °C 7.1: PCC / CH2Cl2 8.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 9.1: 85 percent / DDQ / CH2Cl2; H2O 10.1: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 11.1: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme

1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 2: 85 percent / DDQ / CH2Cl2; H2O 3: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 4: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme

1: 85 percent / DDQ / CH2Cl2; H2O 2: BF3*OEt2; 4 Angstroem MS / CH2Cl2 / 3 h / -20 °C 3: 85 percent / H2 / Pd/C / ethyl acetate; methanol View Scheme