lead(IV) acetate; sodium carbonate in dichloromethane T=-40 - -30°C; Oxidation; 0.333333 h;

1.1: NaIO4; SiO2 / CH2Cl2; H2O / 0.5 h / 20 °C 1.2: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 1.3: 50 percent / tetrahydrofuran; toluene; CH2Cl2 / 4 h / 20 °C 2.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 30 h / 20 °C View Scheme

1: 98 percent / Na2CO3; Pb(OAc)4 / CH2Cl2 / 0.33 h / -40 - -30 °C 2: 85 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C 3: 81 percent / TBAF / tetrahydrofuran 4: 92 percent / CBr4; DIPHOS 5: 96 percent / acetonitrile 6: 70 percent / LiHDMS / tetrahydrofuran / -78 - 20 °C View Scheme

acetic acid T=20°C; 20 h;

quinoline; hydrogenchloride; methanol; hydrogen; Pd-BaSO4 in methanol 1.) 14 h; 2.) 30 min;

hydrogen; triethylamine; Lindlar's catalyst 2.) THF, 23 deg C, 1 atm, 4.5 h; Multistep reaction;

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 View Scheme

1: 82 percent / HMPA, n-butyl lithium / tetrahydrofuran; hexane / 12 h / 0 - 20 °C 2: 94 percent / 1.) hydrogen, quinoline; 2.) 1M HCl/MeOH / 10percent Pd/BaSO4 / methanol / 1.) 14 h; 2.) 30 min View Scheme

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.;