1: 88 percent / H2 / Raney Ni / methanol / 18 h 2: 97 percent / NEt3 / CHCl3 / 1.) 0 deg C, 5 h; 2.) RT 3: 90 percent / TsCl / pyridine / 1.) -10 deg C, 1 h; 2.) 0 deg C, 16 h 4: 26 percent / CF3COOH / CHCl3; methanol / 1.) -5 deg C, 2 h; 2.) RT View Scheme

1: 67 percent / imidazole / CH2Cl2 / 24 h / Ambient temperature 2: aq. KMnO4 / 2-methyl-propan-2-ol / 1.75 h / Ambient temperature; pH 11 (KOH, Na2HPO4) 3: diethyl ether View Scheme