1: 90 percent / KI, K2CO3 / acetone / 16 h / Heating 2: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF 3: 80 percent / H2 / Pd/C / ethyl acetate View Scheme

1: 90 percent / KI, K2CO3 / acetone / 16 h / Heating 2: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF 3: 66 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 4: 76 percent / H2 / Pd/C / ethyl acetate View Scheme

Multi-step reaction with 7 steps 1: 100 percent / pyridine / CH2Cl2 / 1.33 h2: N-bromosuccinimide, benzoyl peroxide / CCl4 / 2 h / Heating3: 56 percent / CH2Cl2; diethyl ether / 48 h4: 100 percent / pyridine / CH2Cl2 / 1.5 h / Ambient temperature6: 95 percent / BF3*Et2O / CH2Cl2 / 0.5 h7: H2 / 10percent Pd-C / ethyl acetate; aq. ethanol / 6 h / 2250.2 Torr / Ambient temperature  

Multi-step reaction with 5 steps 1: 90 percent / KI, K2CO3 / acetone / 16 h / Heating2: 1.) lithium hexamethyldisilylamide (LHDS) / 1.) benzene, 2.) benzene, 0 deg C, 5 min3: 78 percent / 60percent aq. perchloric acid / acetic acid; CH2Cl2 / 4.5 h / Ambient temperature4: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature5: 81 percent / H2 / Pd/C / ethyl acetate / 18 h / 2280 Torr / Ambient temperature  

Multi-step reaction with 2 steps 1: 90 percent / KI, K2CO3 / acetone / 16 h / Heating2: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF  

Multi-step reaction with 3 steps 1: 90 percent / KI, K2CO3 / acetone / 16 h / Heating2: 1.) lithium hexamethylsilylamide (LHDS) / 1.) THF, -80 deg C, 2.) THF3: 66 percent / LiAlH4 / tetrahydrofuran / Ambient temperature