in toluene 3 h; Heating;

1: 60 percent / toluene / 3 h / Heating 2: 1.) n-BuLi; 2.) MnO2 / 1.) THF, hexane, 1 h, r.t.; 2.) CH2Cl2, 2 h View Scheme

1: 60 percent / toluene / 3 h / Heating 2: 1.) n-BuLi; 2.) MnO2 / 1.) THF, hexane, 1 h, r.t.; 2.) CH2Cl2, 2 h View Scheme

1: 1) CuI / 1) THF, -50 deg C, 30 min 2) THF, up to r. t., 10 h 2: 98 percent / tert-butyl hydroperoxide , Ti(i-PrO)4, diethyl (-)tartrate / toluene; CH2Cl2 / 20 h / -30 °C 3: 80 percent / LiAlH4 / diethyl ether / 1a) 0 deg C, 30 min, b) r. t., 10 h 4: I2, 4percent aq. NaHCO3 / CH2Cl2 / 10 h / Ambient temperature 5: 1,5-diazabicyclo<4.3.0>non-5-ene / 10 h / Ambient temperature 6: 84 percent / 1) O3, 2) Me2S / CH2Cl2; methanol / 1) -78 deg C, 45 min, 2) up to r. t., 12 h View Scheme