n-butyllithium; N,N,N',N,-tetramethylethylenediamine 1.) THF, 5-15 deg C, sonication, 2 h, 2.) r.t., several hours; Yield given. Multistep reaction. Yields of byproduct given;

1.1: anhydrous iron chloride / methanol; water / 20 °C 2.1: silver orthophosphate; (NH4)2S2O8 / water; acetonitrile / 85 °C / |Inert atmosphere 3.1: palladium diacetate; triphenylphosphine; potassium carbonate / toluene / 12 h / 110 °C / |Inert atmosphere 3.2: 0.5 h / 95 °C 4.1: ammonium acetate / toluene / 10 h / 120 °C / |Sealed tube; |Darkness View Scheme

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran T=0 - 20°C; methoxymethylation; 2 h;

1: 82 percent / K2CO3 / acetone / 10 h / Heating 2: 65 percent / Et3N, Ph3P / Pd(OAc)2 / 12 h / 80 °C 3: 95 percent / H2 / Pd/C / ethanol 4: 84 percent / (COCl)2 / CH2Cl2; dimethylsulfoxide / 1 h / -78 °C 5: 66 percent / NaNH2 / tetrahydrofuran / 2 h / -78 °C 6: 94 percent / 48percent HBr / ethanol / 1 h 7: 94 percent / Ag2CO3 / benzene / 2 h View Scheme

1: K2CO3 / methanol 2: (i) Li, Et2O, (ii) /BRN= 2014479/, (iii) /BRN= 1209228/ View Scheme

potassium carbonate in methanol

1: K2CO3 / methanol 2: (i) Mg, EtBr, THF, (ii) /BRN= 1209228/ 3: SOCl2 / diethyl ether 4: dimethylsulfoxide 5: aq. KOH / ethane-1,2-diol 7: aq. HClO4 / acetic acid 8: NaOEt / ethanol View Scheme

1: K2CO3 / methanol 2: (i) Mg, EtBr, THF, (ii) /BRN= 1209228/ View Scheme

1: K2CO3 / methanol 2: (i) Li, Et2O, (ii) /BRN= 2014479/, (iii) oxirane View Scheme

1: K2CO3 / methanol 2: (i) Mg, EtBr, THF, (ii) /BRN= 1209228/ 3: SOCl2 / diethyl ether View Scheme