1: 59 percent / Bu3SnH; AIBN 2: 91 percent / DDQ 3: 97 percent / Bu4NF 4: Dess-Martin periodinane 5: 99 percent / Dess-Martin periodinane 6: 74 percent / n-BuLi 7: DIBAL-H 8: Dess-Martin periodinane 9: 67 percent / Li(i-Pr)2N / -78 °C 10: 79 percent / Cl2CHCO2H 11: Dess-Martin periodinane 12: NaClO2 13: MgBr2; n-BuSH; K2CO3 14: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 15: 91 percent / CF3CO2H / CH2Cl2 16: DMDO / -50 °C View Scheme

1: 59 percent / Bu3SnH; AIBN 2: 91 percent / DDQ 3: 97 percent / Bu4NF 4: Dess-Martin periodinane 5: 99 percent / Dess-Martin periodinane 6: 74 percent / n-BuLi 7: DIBAL-H 8: Dess-Martin periodinane 9: 67 percent / Li(i-Pr)2N / -78 °C 10: 79 percent / Cl2CHCO2H 11: Dess-Martin periodinane 12: NaClO2 13: MgBr2; n-BuSH; K2CO3 14: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 15: 91 percent / CF3CO2H / CH2Cl2 View Scheme