1: 80 percent / TEA, DMAP / tetrahydrofuran; dimethylformamide / Heating 2: 1.) O3, 2.) Me2S / 1.) MeOH, - 60 deg C 3: 1.) NaH / 1.) THF 4: 54 percent / dibal / diethyl ether / -78 - 0 °C 5: 1.) Pyr-SO3, 2.) LiAlH4 / 1.) THF View Scheme

1: 1.) CuI / 1.) Et2O 2: 80 percent / TEA, DMAP / tetrahydrofuran; dimethylformamide / Heating 3: 1.) O3, 2.) Me2S / 1.) MeOH, - 60 deg C 4: 1.) NaH / 1.) THF 5: 54 percent / dibal / diethyl ether / -78 - 0 °C 6: 1.) Pyr-SO3, 2.) LiAlH4 / 1.) THF View Scheme

1: 1.) O3, 2.) Me2S / 1.) MeOH, - 60 deg C 2: 1.) NaH / 1.) THF 3: 54 percent / dibal / diethyl ether / -78 - 0 °C 4: 1.) Pyr-SO3, 2.) LiAlH4 / 1.) THF View Scheme

1: 1.) NaH / 1.) THF 2: 54 percent / dibal / diethyl ether / -78 - 0 °C 3: 1.) Pyr-SO3, 2.) LiAlH4 / 1.) THF View Scheme

lithium aluminium tetrahydride; sulfur trioxide pyridine complex 1.) THF; Yield given. Multistep reaction;

hydrogen fluoride in acetonitrile T=0°C;