1: With 2,2'-bis(picolinoyloxy)-(1S)-1,1'-binaphthalene; silver hexafluoroantimonate; copper dichloride in dichloromethane T=-78°C; 3 h; 2: With titanium tetrachloride in dichloromethane T=0°C; 0.5 h; 3: With hydrogenchloride in methanol T=60°C; 12 h; Title compound not separated from byproducts;

pyridine; benzeneselenenyl chloride in dichloromethane T=0°C; Dehydrogenation; 1.5 h;

dihydrogen peroxide in dichloromethane; water T=0°C; 0.416667 h;

2,6-dimethylpyridine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane in tetrahydrofuran T=60°C; P=38787.1 Torr; 48 h;

dihydrogen peroxide in dichloromethane T=0 - 20°C; Oxidation; 1 h;

2,6-dimethylpyridine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane in tetrahydrofuran T=60°C; P=38787.1 Torr; 48 h;

1: 76 percent / LDA / tetrahydrofuran; hexane 2: 84 percent / tosyl azide; KF/Al2O3 / tetrahydrofuran / 24 h / 20 °C 3: 72 percent / Rh2(OAc)4 / CH2Cl2 / 20 °C View Scheme

1: 85 percent / toluene / 1 h / -78 - -40 °C 2: H2 / Lindlar, quinoline (7 percent) / benzene / 2 h / 5 °C / 760 Torr 3: HF- pyridine / acetonitrile / 1 h / 20 °C 5: 28 percent / lithium hydride / dimethylformamide / 3 h / -20 °C / further reagents View Scheme