1: 77 percent / NaI / acetone / 24 h / Heating 2: 1.) Rieke's activated zinc, 2.) 1M HCl / 1.) ether, 20 deg C, 12 h 2.) ether, ice-water bath and room t. View Scheme

1: (i) Na, liq. NH3, Fe(NO3)3, (ii) /BRN= 1098275/ 2: H2 / Pd-BaSO4 / pyridine 3: nBu3SnH, AIBN / benzene / 36 h / Heating View Scheme

1: H2 / Pd-BaSO4 / pyridine 2: nBu3SnH, AIBN / benzene / 36 h / Heating View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 36 h; Heating;

copper(I) bromide dimethylsulfide complex; triethyl phosphite 1.) ether, -40 deg C and 20 min, -35 deg C, 2.) ether, -55 deg C and 30 min, -30 deg C, 3.) ether, HMPA, THF, -30 deg C and room t.; Yield given. Multistep reaction;