1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / |Inert atmosphere 2: phosphorus tribromide / diethyl ether / 0 °C / |Inert atmosphere; |Darkness View Scheme

1: 80 percent / LiAlH4 / diethyl ether / 2 h / -30 °C 2: 81 percent / NEt3 / diethyl ether / 3 h / Ambient temperature 3: NEt3 / PdCl2(PPh3)2 / benzene / 3 h / 140 °C / 38000 Torr / effects of catalysts; also for other substituted 2,4-pentadienyl acetates or o-(bromomethyl)(1-alkenyl)benzenes View Scheme

1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K3[Fe(CN)6]; K2OsO4*2H2O / K2CO3; CH3SO2NH2 / 2-methyl-propan-2-ol / 0 °C 1.2: 8.732 g / p-TsOH*H2O / acetone / 20 °C 2.1: 72 percent / Me3SiCl / diethyl ether; hexane / 6 h / -78 °C 3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 3.2: oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C 4.1: LDA / tetrahydrofuran / 0.33 h / -78 °C 4.2: 85 percent / tetrahydrofuran; dimethylformamide / -78 - 20 °C 5.1: 99 percent / LiAlH4 / tetrahydrofuran / 5 - 20 °C 6.1: 94 percent / DABCO / CH2Cl2 / 20 °C 7.1: 99 percent / NaHCO3 / dimethylsulfoxide / 5 h / 60 °C 8.1: 92 percent / DIBALH / toluene / 2 h / -78 °C 9.1: NaH / tetrahydrofuran / 0 - 20 °C 9.2: 85 percent / tetrahydrofuran / 3 h / -78 °C 10.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C 11.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C 12.1: aq. TFA / CH2Cl2 / 0 - 20 °C 13.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C 14.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C 14.2: AcBr / CH2Cl2 / 4 h / 20 °C 14.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C View Scheme