potassium tert-butylate in tetrahydrofuran; N,N-dimethyl-formamide T=-20 - 20°C; 1 h;

1: 59 percent / t-BuOK / dimethylformamide / 1 h / -50 °C 2: 82 percent / t-BuOK / tetrahydrofuran; dimethylformamide / 1 h / -20 - 20 °C View Scheme

1: With [CpRuCl2(PPh3)]; magnesium T=20°C; Kharasch reaction; 15 h; Inert atmosphere; 2: With diisobutylaluminium hydride; lithium chloride 3: in tetrahydrofuran T=-78 - 20°C; 1 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

bromine; sodium methylate; lithium diisopropyl amide 1.) THF, -78 deg C; 2.) -78 deg C, 30 min, room temp., 12 h, dichloromethane; Yield given. Multistep reaction;

Yield given. Multistep reaction;