1: 89 percent / DBU, LiCl / acetonitrile 2: 94 percent / NEt3, CuI / bis-ditriphenylphosphine palladium chloride / tetrahydrofuran 3: NEt3, CuI / bis-ditriphenylphosphine palladium chloride / tetrahydrofuran 4: MeOH / K2CO3 View Scheme

1: 2) aq. NH4Cl / 1) Et2O 2: PPTS / CH2Cl2 3: 1a) n-BuLi, 2) aq. NH4Cl / 1a) THF, 1b) THF 4: PPTS, EtOH 5: 95 percent / CrO3, aq. H2SO4 / acetone 6: 89 percent / Pd(OAc)2, PPh3 / toluene / 27 h / Heating View Scheme

1: (i) nBuLi, THF, hexane, (ii) /BRN= 1698469/ 2: Cu(OAc)2 / dimethylformamide 3: KOtBu / benzene View Scheme

1: n-decyl-triphenylphosphonium bromide With sodium hexamethyldisilazane in tetrahydrofuran T=-40 - -20°C; 2: 4-pentynal in tetrahydrofuran T=-40 - 0°C; Wittig olefination;

in tetrahydrofuran T=-78°C;

in tetrahydrofuran T=-78°C; 0.166667 h; Inert atmosphere;

in tetrahydrofuran; diethyl ether T=-78°C; Yield given;

in ethanol; water 1.5 h; Ambient temperature;

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 1 h 2: 96 percent / diisobutylaluminum hydride (DIBAL) / tetrahydrofuran; hexane / 0.25 h / 0 °C 3: 81 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / Ambient temperature 4: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, 1 h 5: 1.) cuprous iodide / 1.) THF, ether, 0 deg C, 30 min, 2.) THF, ether, -78 deg C, 2 h 6: 95 percent / Amberlyst-15 resin (H+ form), methanol / 3 h / Ambient temperature View Scheme

1.1: sodium hydride / diethyl ether; mineral oil / 0 °C 1.2: 0 °C 2.1: diisobutylaluminium hydride / diethyl ether / 0 °C 3.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C 4.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C 5.2: -78 - 20 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C 6.2: 2 h / 0 °C View Scheme