1: 96 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) r.t., 14 h 2: 92 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: diethyl ether; cyclohexane / 0 deg C, 35 min, 0 deg C to rt, rt, 19 h 2: 82 percent / (nBu)4NF / tetrahydrofuran / 0 deg C to rt, rt, 17 h View Scheme

1H-imidazole in N,N-dimethyl-formamide T=0°C; 0.166667 h;

1: 72 percent / 48percent HBr / 72 h / 90 °C 2: 82 percent / Et3N, DMAP / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: Amberlyst 50 / methanol View Scheme

1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min 2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C 6: 89 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 18 h / Ambient temperature 7: 99 percent / H2O, AcOH / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min 2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C 6: diethyl ether / 1 h 7: 81 percent / H2O, AcOH / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min 2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C 6: diethyl ether / 1 h View Scheme