diisobutylaluminium hydride in hexane; dichloromethane T=-78 - 22°C; 16 h;

diethylzinc; CuCN in tetrahydrofuran

methanol; CuCN in tetrahydrofuran T=25°C;

platinum (II) chloride; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in tetrahydrofuran T=50°C; 12 h; Inert atmosphere; regioselective reaction;

HPtCl6·6H2O in tetrahydrofuran T=50°C; 5 h; Inert atmosphere; stereoselective reaction;

1: 14 percent / 1,1,1,3,3,3-hexamethyldisilazane, BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min, 2.) -78 deg C, 15 min, 3.) -78 deg C, 1 h 2: 81 percent / DIBAL / toluene; CH2Cl2 / 1.5 h View Scheme

1: 1.) t-BuLi, 3.) 0.2 M HCl / 1.) THF, pentane, -65 deg C to 0 deg C, 15 min, 2.) -65 deg C to room temperature, 14 h, 3.) acetone, H2O, 1 h 2: 14 percent / 1,1,1,3,3,3-hexamethyldisilazane, BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min, 2.) -78 deg C, 15 min, 3.) -78 deg C, 1 h 3: 81 percent / DIBAL / toluene; CH2Cl2 / 1.5 h View Scheme

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