1: 67 percent / CuCl2, PdCl2 / H2O; dimethylformamide / 10 h / Ambient temperature 2: 65 percent / aq. NaOH / ethanol / 5 h / Heating View Scheme

1: 90 percent / diisobutyl aluminum hydride / diethyl ether; hexane / 1 h / 0 °C 2: 1.) diisopropyl D-(-)-tartrate, titanium tetraisopropoxide, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -22 deg C, 1 h, 2.) CH2Cl2, isooctane, -20 deg C, 20 h 3: 68 percent / titanium tetraisopropoxide / CH2Cl2 / 24 h / Heating 4: 1.) NaIO4, RuCl3, 2.) NaHCO3 / 1.) CH3CN, CCl4, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h View Scheme

1: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) aq. NaOH, 30percent aq. H2O2 / 1.) THF, RT, 5 h, 2.) THF, 50 deg C, 1 h 2: 62 percent / aq. NaOH / ethanol / 5 h / Heating View Scheme

1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride in acetonitrile T=20°C; Horner-Wadsworth-Emmons reaction;

sodium hydride in tetrahydrofuran; hexane 3 h; Ambient temperature;

copper dichloride; palladium dichloride in water; N,N-dimethyl-formamide 10 h; Ambient temperature;

sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1.) THF, RT, 5 h, 2.) THF, 50 deg C, 1 h; Yield given. Multistep reaction;