1: 77 percent / 1N NaOH / dimethylformamide; methanol / 18 h / 60 °C 2: 65 percent / tetrahydrofuran; acetone / 1.) -15 deg C, 3h, 2.) 25 deg C, 18h 3: 100 percent / pyridine, hydroxylamine hydrochloride / methanol / 1 h / Heating 4: 95percent hydrazine hydrate / methanol / 72 h / Heating 5: 4 h / Heating 6: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 7: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 8: 0.1 N NaOH / acetonitrile / 18 h / 25 °C 9: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 98 percent / tetrahydrofuran / 4 h / Heating 2: 77 percent / 1N NaOH / dimethylformamide; methanol / 18 h / 60 °C 3: 65 percent / tetrahydrofuran; acetone / 1.) -15 deg C, 3h, 2.) 25 deg C, 18h 4: 100 percent / pyridine, hydroxylamine hydrochloride / methanol / 1 h / Heating 5: 95percent hydrazine hydrate / methanol / 72 h / Heating 6: 4 h / Heating 7: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 8: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 9: 0.1 N NaOH / acetonitrile / 18 h / 25 °C 10: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 1.) diisopropylamine, BuLi, 3.) CO2, Br2 2: 2.) aq. KI3 View Scheme

I2 Yield given. Multistep reaction;