1: 80 percent / pyridine 2: 59 percent / Bu3SnH; AIBN 3: 91 percent / DDQ 4: 97 percent / Bu4NF 5: Dess-Martin periodinane 6: 99 percent / Dess-Martin periodinane 7: 74 percent / n-BuLi 8: DIBAL-H 9: Dess-Martin periodinane 10: 67 percent / Li(i-Pr)2N / -78 °C 11: 79 percent / Cl2CHCO2H 12: Dess-Martin periodinane 13: NaClO2 14: MgBr2; n-BuSH; K2CO3 15: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 16: 91 percent / CF3CO2H / CH2Cl2 17: DMDO / -50 °C View Scheme

1: 80 percent / pyridine 2: 59 percent / Bu3SnH; AIBN 3: 91 percent / DDQ 4: 97 percent / Bu4NF 5: Dess-Martin periodinane 6: 99 percent / Dess-Martin periodinane 7: 74 percent / n-BuLi 8: DIBAL-H 9: Dess-Martin periodinane 10: 67 percent / Li(i-Pr)2N / -78 °C 11: 79 percent / Cl2CHCO2H 12: Dess-Martin periodinane 13: NaClO2 14: MgBr2; n-BuSH; K2CO3 15: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 16: 91 percent / CF3CO2H / CH2Cl2 View Scheme