HIO4*2H2O in tetrahydrofuran; diethyl ether T=0°C; 0.5 h; Inert atmosphere;

1: 93 percent / aluminium isopropoxide / toluene / 8 h / Heating 2: 78 percent / t-BuOOH / 2.) VO(acac)2 / benzene / 4 h / Ambient temperature 3: 63 percent / copper(I) iodide / diethyl ether / 4 h / 0 °C 4: 1.) N,N-dimethylformamide dimethyl acetale / 1.) rt., overnight; 2.) acetic anhydride, boiling, 8 h 5: 84 percent / LiNH2 / liquid ammonia; hexane / 0.5 h View Scheme

2: KN(SiMe3)2 / toluene / -78 °C 3: DIBAL / toluene / -78 °C 4: H2O, SiO2 5: 95 percent / NaBH4 / methanol 6: 74 percent / Li, EtNH2 / -78 °C View Scheme