1: 91 percent / DDQ 2: 97 percent / Bu4NF 3: Dess-Martin periodinane 4: 99 percent / Dess-Martin periodinane 5: 74 percent / n-BuLi 6: DIBAL-H 7: Dess-Martin periodinane 8: 67 percent / Li(i-Pr)2N / -78 °C 9: 79 percent / Cl2CHCO2H 10: Dess-Martin periodinane 11: NaClO2 12: MgBr2; n-BuSH; K2CO3 13: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 14: 91 percent / CF3CO2H / CH2Cl2 15: DMDO / -50 °C View Scheme

1: 91 percent / DDQ 2: 97 percent / Bu4NF 3: Dess-Martin periodinane 4: 99 percent / Dess-Martin periodinane 5: 74 percent / n-BuLi 6: DIBAL-H 7: Dess-Martin periodinane 8: 67 percent / Li(i-Pr)2N / -78 °C 9: 79 percent / Cl2CHCO2H 10: Dess-Martin periodinane 11: NaClO2 12: MgBr2; n-BuSH; K2CO3 13: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 14: 91 percent / CF3CO2H / CH2Cl2 View Scheme