1: 85 percent / (-)-9-pinanyl-BBN / tetrahydrofuran / 25 °C 2: 80 percent / KF.2H2O / dimethylformamide 3: 96 percent / imidazole / dimethylformamide 4: 93 percent / Et2NH, Pd(PPh3)4, CuI / 15 h / Ambient temperature 5: 92 percent / PPh3, CBr4 / CH2Cl2 / -40 - 0 °C 6: 90 percent / 100 °C 7: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h 8: 60 percent / H2 / Lindlar catalyst / CH2Cl2 / 22 h / Ambient temperature 9: 73 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature View Scheme

Na2B4O7 in methanol 0.166667 h; Ambient temperature;

aluminium trichloride in dichloromethane T=-10°C; 3 h;