toluene-4-sulfonic acid in benzene Heating;

1: 1.) LDA / 1.) THF, hexane, 0 deg C, 4 h, 2.) THF, hexane, 0 deg C, 1 h 2: 87 percent / p-TsOH*H2O / benzene / 2 h / Heating View Scheme

1: 1.) LDA / 1.) THF, hexane, 0 deg C, 4 h, 2.) THF, hexane, 0 deg C, 1 h 2: 87 percent / p-TsOH*H2O / benzene / 2 h / Heating View Scheme

sodium hydride in tetrahydrofuran

1: 77 percent / TiBr2(i-PrO2)2, (4R,5R)-α,α,α',α'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol, mol. sieves 4A / CH2Cl2 / 20 h / -70 °C 2: 95 percent / HCl / tetrahydrofuran / 2 h / Ambient temperature 3: H2, 10percent Pd-C / tetrahydrofuran; ethanol 4: n-Bu3SnH, AIBN / benzene / 4 h / Heating View Scheme

n-butyllithium; ClB(OMe)3; sodium salt of 3-chloroperoxybenzoic acid 1.) hexane, -78 degC, warm to 20 degC, 0.25 h at -20 degC then 1 h at room temperature; 2.) methylene chloride/hexane, 1 h, -20 degC; Yield given. Multistep reaction;