1: SOCl2 / benzene / 4 h 2: diethyl ether / Ambient temperature 3: 31 percent / CuSO4 / cyclohexane / 4 h / Heating View Scheme

copper(II) sulfate in cyclohexane 4 h; Heating;

1: diethyl ether / Ambient temperature 2: 31 percent / CuSO4 / cyclohexane / 4 h / Heating View Scheme

dirhodium tetraacetate in methanol; dichloromethane T=0°C; 1 h;

1,1'-bis(diphenylphosphino)ferrocene-Pd in tetrahydrofuran T=25°C; 4 h; Yield given. Yields of byproduct given;

dirhodium tetraacetate in dichloromethane T=0°C; 1 h;

1: 80 percent / conc. HCl / 0.02 h / Heating 2: 1.) TMEDA, n-BuLi / 1.) hexanes, a.) -78 deg C, 60 min b.) RT, 1.5h; 2.) RT 3h. 3: diisobutylammonium hydride / CH2Cl2; hexane / 3 h / -78 °C 4: 75 percent / triethylamine, DMAP / CH2Cl2 / 0.5 h / 0 °C 5: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 6: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 7: 5percent aq. NaOH 8: diethyl ether / 0.5 h / 0 °C View Scheme

1: 1.) TMEDA, n-BuLi / 1.) hexanes, a.) -78 deg C, 60 min b.) RT, 1.5h; 2.) RT 3h. 2: diisobutylammonium hydride / CH2Cl2; hexane / 3 h / -78 °C 3: 75 percent / triethylamine, DMAP / CH2Cl2 / 0.5 h / 0 °C 4: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 5: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 6: 5percent aq. NaOH 7: diethyl ether / 0.5 h / 0 °C View Scheme

1: diisobutylammonium hydride / CH2Cl2; hexane / 3 h / -78 °C 2: 75 percent / triethylamine, DMAP / CH2Cl2 / 0.5 h / 0 °C 3: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 4: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 5: 5percent aq. NaOH 6: diethyl ether / 0.5 h / 0 °C View Scheme

1: 75 percent / triethylamine, DMAP / CH2Cl2 / 0.5 h / 0 °C 2: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 3: 1.) LDA / 1.) hexane, THF, -78 deg C, 10 min, 2.) reflux, 2h 4: 5percent aq. NaOH 5: diethyl ether / 0.5 h / 0 °C View Scheme