1: dimethylformamide 2: (i) K, HMPT, (ii) /BRN= 1753213/ View Scheme

1: 1.) Mg / 1.) ether, 2.) ether, 8 h, RT 2: 54 percent / I2 / CHCl3 / 2 h / Heating 3: 1.) O3, 2.) LiAlH4 / 1.) hexane, -45 deg C, 2.) hexane, ether, from -45 to -35 deg C 4: 94 percent / Br2, NaHCO3, HMPA / CH2Cl2 / 0 °C 5: 95 percent / TosOH*H2O / toluene / 2 h / Heating 6: 90 percent / pyridine / 40 h / 4 °C 7: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 8: 98 percent / 2 h / Heating 9: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 10: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 11: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 12: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 13: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 1-bromo-6-methylheptane With magnesium 2: acrylic acid methyl ester With 4-(N,N-dimethlyamino)pyridine; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex in tetrahydrofuran T=-78°C; 3.5 h;

bromine; triphenylphosphine in dichloromethane T=0°C; 2 h;

acetic acid; zinc 1.) THF, r.t., 10 h, 2.) THF, 12 h; Yield given. Multistep reaction;

lithium bromide in N,N-dimethyl-formamide T=20°C;

1: HBr / 100 °C 2: 1.) Zn, 2.) AcOH / 1.) THF, r.t., 10 h, 2.) THF, 12 h View Scheme

1: diethyl ether 2: H2SO4; HBr View Scheme

1: (i) Mg, (ii) /BRN= 102382/, benzene 2: HBr View Scheme

1: lithium aluminium tetrahydride / diethyl ether / 12 h / Reflux 2: bromine; triphenylphosphine / dichloromethane / 2 h / 0 °C View Scheme