1: Pseudomonas cepacia lipase; NaOH / aq. phosphate buffer; acetone / pH 7.0 - 7.2 2: N-methylmorpholine N-oxide; OsO4; H2O / acetone / 24 h / 20 °C 3: 20.16 g / p-TSA / acetone / 20 h / 20 °C 4: 93 percent / KCN / methanol / 2 h / 20 °C 5: 76 percent / pyridinium chlorochromate; Celite / CH2Cl2 / 15 h / 20 °C 6: 84 percent / sodium borohydride; CeCl3*7H2O / methanol / 0.75 h / 0 °C 7: 72 percent / imidazole / dimethylformamide / 12 h / 20 °C 8: KOH; KMnO4; MgSO4 / methanol; H2O / 2 h / 0 °C 9: 710 mg / sodium borohydride / propan-2-ol / 1 h / 0 °C 10: 85 percent / pyridine / CH2Cl2 / 0 - 20 °C 11: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 12: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 55 °C 13: 980 mg / NH3 / methanol / 48 h / 110 °C 14: 84 percent / trifluoroacetic acid; H2O / 2 h / 20 °C View Scheme

sodium hydroxide; Pseudomonas cepacia lipase in phosphate buffer; acetone pH=7.0 - 7.2;

1: 45 percent / Pseudomonas cepacia lipase; NaOH / aq. phosphate buffer; acetone / pH 7.0 - 7.2 2: 90 percent / pyridine / CH2Cl2 / 0 - 20 °C View Scheme