1: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h 2: 1.) 2percent O3 in O2; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h 3: 1.) isobutylmagnesium bromide; 2.) C5H5TiCl2 / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h View Scheme

1: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h 2: 1.) 2percent O3 in O2; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h 3: 1.) isobutylmagnesium bromide; 2.) C5H5TiCl2 / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h 4: 90 percent / pyridine View Scheme

1: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h 3: 92 percent / H2, quinoline / Lindlar catalyst (Pd-CaCO3-PbO) / hexane / 0.5 h / 10 °C 4: 83 percent / pyridinium tosylate / acetone; H2O / 2.5 h / Heating View Scheme

1: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h View Scheme

1: 53 percent / sodium iodide, zinc dust / tetrahydrofuran / 1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h 2: 1.) 2percent O3 in O2; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h View Scheme

With  sodium iodide; zinc in  tetrahydrofuran  1.) 65-70 deg C, 3 h; 2.) 20 deg C, 3 h;