1.1: 89 percent / imidazole; DMAP / CH2Cl2 / 20 °C 2.1: pyridine; Pb(OAc)4 / CH2Cl2 / 0.25 h / 0 °C 2.2: 83 percent / CeCl3*7H2O; NaBH4 / methanol / 0.25 h / 0 °C 3.1: 81 percent / Amberlite<*> IR-118 ion-exchange resin; Na; EtOH / diethyl ether / 2.5 h / 0 °C 4.1: 72 percent / PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 25 h / 0 - 20 °C 5.1: 73 percent / H2O2 / (NH4)6Mo7O24*4H2O / aq. ethanol / 240 h / 20 °C 6.1: NaHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C 6.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6.3: diethyl ether; tetrahydrofuran / -100 - 20 °C 7.1: Bu4NF*3H2O / tetrahydrofuran / 20 °C / overnight View Scheme

1: 83.3 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 2: 1.) Pb(OAc)4, 2.) NaAlH2(OCH2CH2OCH3)2 / 1.) CH2Cl2, -15 deg C, 15 min, 2.) toluene, RT, 2 h 3: 93 percent / imidazole / CH2Cl2; dimethylformamide / 1.) RT, 15 h, 2.) 45 deg C, 20 h, 3.) 80 deg C, 6 h 4: 1.) ozone, 2.) NaBH4 / 1.) MeOH, pyridine, CH2Cl2, -78 deg C, 1 h, 2.) RT, 12 h 5: 95 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 83.3 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 2: 1.) Pb(OAc)4, 2.) NaAlH2(OCH2CH2OCH3)2 / 1.) CH2Cl2, -15 deg C, 15 min, 2.) toluene, RT, 2 h 3: 93 percent / imidazole / CH2Cl2; dimethylformamide / 1.) RT, 15 h, 2.) 45 deg C, 20 h, 3.) 80 deg C, 6 h 4: 1.) ozone, 2.) NaBH4 / 1.) MeOH, pyridine, CH2Cl2, -78 deg C, 1 h, 2.) RT, 12 h 5: 95 percent / pyridine / 2 h / 0 °C View Scheme

1H-imidazole; 4-(N,N-dimethlyamino)pyridine in dichloromethane T=20°C; Etherification;