1: 91 percent / 2,6-lutidine / CH2Cl2 / -78 °C 2: 99 percent / DDQ; H2O / CH2Cl2 / 0 °C 3: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 4: 98 percent / CeCl3 / tetrahydrofuran / -50 °C 5: 95 percent / Dess-Martin periodinane / CH2Cl2 / 0 °C 6: 63 percent / NaI; AcOH / 20 °C 7: 81 percent / aq. HF; pyridine / acetonitrile / 0 °C 8: 99 percent / Me4NB(OAc)3H / acetic acid; acetonitrile / -30 °C 9: 88 percent / 2,6-lutidine / CH2Cl2 / -78 °C 10: 88 percent / Pd(MeCN)2Cl2 / dimethylformamide / 0 °C 11: tetrazole / CH2Cl2 / 0 °C 12: t-BuOOH / CH2Cl2 / 0 °C 13: HCO2NH2; PPh3 / Pd(PPh3)4 / tetrahydrofuran 14: 79 percent / aq. HF; pyridine / acetonitrile View Scheme