1: (i) LiAlH4, Et2O, (ii) DDQ, dioxane 2: Py 3: 400 °C View Scheme

1: 1.) Br2; 2.) LiBr/Li2CO3 / 1.) CHCl3, RT, 1 h; 2.) DMF, 125-130 deg C, 45 min 2: 37 percent / CrO3/tert-BuOH/Ac2O / CCl4 / 72 h / Heating 3: 1.) H2; 2.) NaBH4 / 1.) RhCl(PPh3)3 / 1.) benzene/EtOH, 2-3 d; 2.) MeOH, -20 - -18 deg C, 30 min 4: 11.4 mg / 1.) 3 N NaOH; 2.) 3 N HCl / tetrahydrofuran / 1.) RT, 30 min; 2.) 1 h 5: 73 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) / dioxane / 27 h / Heating 6: 19 percent / 1.) lithium diisopropylamide (LDA); 2.) hexamethylphosphoramide (HMPA) / tetrahydrofuran / -78 °C / 1.) 30 min; 2.) 3 h 7: 37 percent / 35percent H2O2 / tetrahydrofuran / 0.5 h / 0 °C View Scheme