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

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