polystyrene-supported gallium trichloride#10; in dichloromethane T=20°C; 0.75 h;

sodium azide in N,N-dimethyl-formamide T=20°C;

1: sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 2.5 h / 5 °C / Inert atmosphere 2: toluene-4-sulfonic acid / tert-butyl methyl ether / 3 h / Inert atmosphere; Reflux 3: sodium hydride / N,N-dimethyl-formamide / 4 h / 40 °C / Inert atmosphere 4: hydrogenchloride / water; acetone / Inert atmosphere View Scheme

2: 84 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 2 h / Ambient temperature 3: 1.) sodium hydride / 1.) DMF, 80 deg C, 2.5 h, 2.) DMF, 80 deg C, 24 h View Scheme

1: NaI / acetone / 2 h / Heating 2: PPTS / CH2Cl2 / Ambient temperature 3: 1) bipyridyl, n-BuLi / 1) THF, hexane, -78 deg C, 1h, 2) HMPA, RT, 24h 4: 1) disiamylborane, 2) HOAc / 1) THF, 0 deg C, 1h, 2) RT, 4h 5: 71 percent / 3N HCl / methanol / 1.5 h / Ambient temperature 6: 88 percent / pyridine / acetonitrile / 1 h / 0 °C 7: 43 percent / t-BuOOH, D-(-)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 16 h / -21 °C 8: t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / -21 °C 9: PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C 10: 1N NaOH / methanol / 1 h / 0 °C 11: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O, 0 deg C 12: imidazole / dimethylformamide / Ambient temperature 13: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 14: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme