1.1: H2; ethanolic NH3 / Raney-Co 2.1: Et3N / tetrahydrofuran / 0 °C 3.1: 86 percent / NaOAc; Br2 / 0 °C 4.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C 5.1: NaH / dimethylformamide / 0 °C 5.2: 96 percent / dimethylformamide / 0 °C 6.1: 80 percent / various solvent(s) / 200 - 205 °C 7.1: O3 / methanol / -78 °C 7.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C 8.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C 9.1: pyridine / 0.83 h / -10 - -5 °C 9.2: 86 percent / Et3N / ethyl acetate / Heating View Scheme