1: 1) KOH / 1) DMSO, 50 deg C, 20 min, 2) DMSO, 50 deg C, 30 min 2: 67.9 percent / 30percent H2O2 / acetic anhydride / Ambient temperature View Scheme

1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 4.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating View Scheme

1.1: 70 percent / NaH / dimethylsulfoxide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 5.1: aq. HCl / diethyl ether / 15 h / 20 °C 6.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme

sodium hydride in dimethyl sulfoxide T=0 - 20°C; 15 h;

1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C View Scheme