Dess-Martin periodane in dichloromethane T=20°C; 30 h;

1: (2RS,4Z)-4-decen-1,2-diol With sodium periodate; silica gel in dichloromethane; water T=20°C; 0.5 h; 2: With potassium hexamethylsilazane in tetrahydrofuran; toluene T=-78°C; Wittig reaction; 1 h; 3: ((E)-4-Hydroxy-but-2-enyl)-triphenyl-phosphonium; bromide in tetrahydrofuran; dichloromethane; toluene T=20°C; 4 h; Further stages.;

lithium aluminium tetrahydride in diethyl ether T=-40°C; 1.5 h;

hydrogen; Lindlar's catalyst in methanol T=20°C;

1.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 1.2: 90 percent / tetrahydrofuran; toluene / 2.25 h / -78 - 0 °C 2.1: 92 percent / aq. AcOH / 20 h / 20 °C 3.1: NaIO4; SiO2 / CH2Cl2; H2O / 0.5 h / 20 °C 3.2: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 3.3: 50 percent / tetrahydrofuran; toluene; CH2Cl2 / 4 h / 20 °C View Scheme

1.1: 92 percent / aq. AcOH / 20 h / 20 °C 2.1: NaIO4; SiO2 / CH2Cl2; H2O / 0.5 h / 20 °C 2.2: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.3: 50 percent / tetrahydrofuran; toluene; CH2Cl2 / 4 h / 20 °C View Scheme

potassium carbonate in methanol T=23°C; 3 h; Yield given;

1.1: EtMgBr; CuCl / diethyl ether / 2 h / 20 °C 1.2: 28 percent / diethyl ether / 24 h / Heating 2.1: H2 / Lindlar's catalyst / methanol / 20 °C View Scheme

1.1: 67 percent / PBr3; pyridine / diethyl ether / 2 h / 20 °C 2.1: EtMgBr; CuCl / diethyl ether / 2 h / 20 °C 2.2: 28 percent / diethyl ether / 24 h / Heating 3.1: H2 / Lindlar's catalyst / methanol / 20 °C View Scheme

1: 53 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 4 h; 2.) 27 deg C, 40 h 2: 83 percent / hydrogen / Pd/BaSO4 / methanol / 30 h 3: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 4: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C 5: 69 percent / 7 h / Heating 6: 47 percent Chromat. / Al2O3 / benzene / 1 h / Heating 7: 58 percent / LiAlH4 / diethyl ether / 1.5 h / -40 °C View Scheme