1: 90 percent / tBuOOH, D-(-)-diisopropyl tartrate, Ti(OiPr)4 2: 63 percent / DIBAL / toluene; hexane / 1.) -78 deg C, 2 h, then to 25 deg C over 1 h, 2.) reflux, 0.5 h 3: 100 percent / 1.5 percent methanolic HCl / CH2Cl2 / 0.08 h / 25 °C 4: 100 percent / pyridine, DMAP / 0.25 h / 25 °C 5: 1.) tert-butyldimethylsilyl triflate, 2.) methanolic ammonia / 1.) CH3CN, 25 deg C, 12 h, 2.) 25 deg C, 3 h View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=60°C; 2.5 h;

silica gel; diisobutylaluminium hydride in diethyl ether

diisobutylaluminium hydride in diethyl ether; hexane 2 h;

1: Br2 / 0 °C 2: 62 percent / NaNH2/Fe(NO3)3/NH3(l) / 2 h / -70 °C 3: 56 percent / EtMgBr / tetrahydrofuran / 10 h / 60 °C 4: 82 percent / LiAlH4 / tetrahydrofuran / 2.5 h / 60 °C View Scheme

1: 62 percent / NaNH2/Fe(NO3)3/NH3(l) / 2 h / -70 °C 2: 56 percent / EtMgBr / tetrahydrofuran / 10 h / 60 °C 3: 82 percent / LiAlH4 / tetrahydrofuran / 2.5 h / 60 °C View Scheme