in diethyl ether 16 h; cooling;

magnesium in diethyl ether 2h, 0 deg C -> 3h, r.t.;

1: 1.) boron trifluoride etherate, molecular sieve 4A / 1.) toluene, reflux, 40 h; 2.) THF, RT, 24 h 2: 62 percent / lithium diisopropylamide / 1.) THF, -78 deg C, 5 min; 2.) -50 deg C, 4 h 3: 100 percent / potassium hydroxide / ethane-1,2-diol / Heating View Scheme

triethylamine in 1,4-dioxane 1.5 h; Heating / reflux;

1.1: triethylamine / benzene / 2 h 1.2: 3.5 h / 90 °C / Reflux 2.1: N-bromosuccinmide / acetonitrile / Reflux 3.1: trichlorophosphate / 5 h / Reflux 3.2: -35 °C / pH 8 4.1: n-butyllithium; tri-isopropoxy-borane / hexane; tetrahydrofuran / 0.75 h / -78 - -65 °C 4.2: 1.17 h / -60 - 20 °C 4.3: 0 °C / pH 6 5.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C 6.1: potassium tert-butylate / dimethyl sulfoxide / 10 - 20 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / 16 h 8.1: hydrogenchloride / water; methanol / 2 h / Reflux 9.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 0 - 20 °C View Scheme

hydrogenchloride; triethylamine in hexane; toluene

1: With triethylamine in benzene 2 h; 2: in bis-maleimidodiphenyl-methane acid T=90°C; 3.5 h; Reflux;

sodium tetrahydroborate; lithium chloride in tetrahydrofuran T=0 - 35°C; 0.5 h;

1: 1.) boron trifluoride etherate, molecular sieve 4A / 1.) toluene, reflux, 40 h; 2.) THF, RT, 24 h 2: 31 percent / potassium hydroxide / ethanol / 24 h / Heating View Scheme

in tetrahydrofuran T=65°C; 18 h;