1: 54.3 percent / NBA, 70 percent HClO4 / dioxane; H2O / 2 h / Ambient temperature 2: Pb(AcO)4, I2, CaCO3 / cyclohexane / 1 h / Heating; Irradiation View Scheme

1: 1.8 g / lithium tri-tert-butoxyaluminium hydride / tetrahydrofuran / 0.67 h / Ambient temperature 2: 1.8 g / pyridine / 24 h / Ambient temperature 3: 2.1 g / KOH / methanol; tetrahydrofuran / 1.5 h / 16 °C 4: 5.8 g / Jones' reagent / acetone / 0.25 h 5: 4.02 g / NaHCO3 / pyridine; H2O / 2.5 h / 100 °C 6: 3.3 g / Zn / acetic acid / 0.75 h / 90 °C View Scheme

1: Zn 2: TsOH 3: Br2 / acetic acid 4: NaOMe 5: TsOH View Scheme

zinc in acetic acid T=45°C; 1 h; Yield given;

in ethanol