1: 3-chloroprop-1-ene With iodine; magnesium in diethyl ether T=0 - 20°C; 2: 2,6,6-Trimethyl-3-isobutoxycyclohex-2-en-1-one in tetrahydrofuran; diethyl ether T=20°C;

1: 86 percent / OsO4; N-methylmorpholine N-oxide / acetone; H2O; 2-methyl-propan-2-ol / 20 °C 2: 93 percent / NaIO4 / diethyl ether; H2O / 1 h 3: 91 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 56 percent / MnO2 / CHCl3 / 43 h / 20 °C View Scheme

1: 86 percent / OsO4; N-methylmorpholine N-oxide / acetone; H2O; 2-methyl-propan-2-ol / 20 °C 2: 93 percent / NaIO4 / diethyl ether; H2O / 1 h 3: 91 percent / LiAlH4 / tetrahydrofuran / 0 °C View Scheme