sodium hydroxide in methanol 24 h; Heating;

1.1: Mg / tetrahydrofuran 1.2: 95 percent / MeMgCl; Li2CuCl4 / tetrahydrofuran / 16 h / -20 - 20 °C 2.1: 77 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / 20 °C 3.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 3.2: tetrahydrofuran / 16 h / -20 - 20 °C 4.1: 42.86 g / diethyl ether 5.1: H2 / 10 percent Pd/C / ethyl acetate 6.1: TsOH / methanol / 20 °C 7.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1.1: 36 percent / aq. HBr / 22 h / 80 °C 2.1: 96 percent / conc. HCl / 2.5 h / 20 °C 3.1: Mg / tetrahydrofuran 3.2: 95 percent / MeMgCl; Li2CuCl4 / tetrahydrofuran / 16 h / -20 - 20 °C 4.1: 77 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / 20 °C 5.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 5.2: tetrahydrofuran / 16 h / -20 - 20 °C 6.1: 42.86 g / diethyl ether 7.1: H2 / 10 percent Pd/C / ethyl acetate 8.1: TsOH / methanol / 20 °C 9.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1.1: 96 percent / conc. HCl / 2.5 h / 20 °C 2.1: Mg / tetrahydrofuran 2.2: 95 percent / MeMgCl; Li2CuCl4 / tetrahydrofuran / 16 h / -20 - 20 °C 3.1: 77 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / 20 °C 4.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 4.2: tetrahydrofuran / 16 h / -20 - 20 °C 5.1: 42.86 g / diethyl ether 6.1: H2 / 10 percent Pd/C / ethyl acetate 7.1: TsOH / methanol / 20 °C 8.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1.1: NaOEt / ethanol 1.2: ethanol / 21 h / Heating 1.3: 80 percent / aq. HBr; H2SO4 / acetic acid / Heating 2.1: 100 percent / 15 h / 140 °C 3.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 3.2: tetrahydrofuran / 16 h / -20 - 20 °C 4.1: 42.86 g / diethyl ether 5.1: H2 / 10 percent Pd/C / ethyl acetate 6.1: TsOH / methanol / 20 °C 7.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1.1: 100 percent / 15 h / 140 °C 2.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 2.2: tetrahydrofuran / 16 h / -20 - 20 °C 3.1: 42.86 g / diethyl ether 4.1: H2 / 10 percent Pd/C / ethyl acetate 5.1: TsOH / methanol / 20 °C 6.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 1.2: tetrahydrofuran / 16 h / -20 - 20 °C 2.1: 42.86 g / diethyl ether 3.1: H2 / 10 percent Pd/C / ethyl acetate 4.1: TsOH / methanol / 20 °C 5.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1.1: 77 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / 20 °C 2.1: (Me3Si)2NNa / tetrahydrofuran / 1.5 h 2.2: tetrahydrofuran / 16 h / -20 - 20 °C 3.1: 42.86 g / diethyl ether 4.1: H2 / 10 percent Pd/C / ethyl acetate 5.1: TsOH / methanol / 20 °C 6.1: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1: H2 / 10 percent Pd/C / ethyl acetate 2: TsOH / methanol / 20 °C 3: 95 percent / NaOH / methanol / 24 h / Heating View Scheme

1: TsOH / methanol / 20 °C 2: 95 percent / NaOH / methanol / 24 h / Heating View Scheme