1: 100 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 8 h / Ambient temperature 2: water, NaOH / 47 h / 0 - 5 °C / cholesterol esterase from bovine pancreas, pH 7.8 3: NaOMe / methanol / 1 h / 0 - 5 °C 4: 1.) 80percent CH3COOH 2.) NaOCH3 / 1.) heating, 2.) methanol View Scheme

1: 100 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 8 h / Ambient temperature 2: water, NaOH / 47 h / 0 - 5 °C / cholesterol esterase from bovine pancreas, pH 7.8 3: NaOMe / methanol / 1 h / 0 - 5 °C 4: 1.) 80percent CH3COOH 2.) NaOCH3 / 1.) heating, 2.) methanol 5: 97 percent / NaOH / tetrahydrofuran; H2O / 5.5 h / Ambient temperature View Scheme

1: 100 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 8 h / Ambient temperature 2: water, NaOH / 47 h / 0 - 5 °C / cholesterol esterase from bovine pancreas, pH 7.8 3: NaOMe / methanol / 1 h / 0 - 5 °C 4: 100 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature 5: dimethyl diazomalonate, rhodium octanoate dimer / benzene / 0.5 h / Ambient temperature View Scheme