1.1: 81 percent / tetrahydrofuran / 2.5 h / -40 - 20 °C 2.1: ZnBr2 / CH2Cl2 / 20 °C 3.1: 678 mg / SmI2; HMPA / tetrahydrofuran; methanol / 0 - 20 °C 4.1: LiAlH4 / tetrahydrofuran / 3 h / 65 °C 5.1: 195 mg / TEA; DMAP / CH2Cl2 / 20 °C 6.1: 90 percent / NaH / dimethylformamide / 4 h / 0 °C 7.1: O3 / methanol / -78 °C 7.2: 92 percent / Me2S / methanol / -78 - 20 °C 8.1: DIPEA; TMSOTf / CH2Cl2 / 0.33 h / 20 °C 8.2: NBS / CH2Cl2 / 1 h / 20 °C 9.1: 78 mg / KH / dimethylformamide / 10.5 h / 0 - 70 °C 10.1: 92 percent / HCl / 26 h / Heating View Scheme