boron trifluoride diethyl etherate in tetrahydrofuran; diethyl ether T=-78 - 20°C; 8 h; Yields of byproduct given;

1: AlCl3 2: Zn/HCl 3: CF3COOH, (CF3COO)2O 4: 2.) 10percent HCl / 1.) Et2O, reflux, 4 h, 2.) CH2Cl2 5: 1.) N-methylmorpholine N-oxide, OsO4, 2.) sodium dithionite, 3.) 6N HCl / 1.) Me2CO, t-BuOH, 2 d, 2.) 1 h, 3.) CH2Cl2 6: 55 percent / Pd/C / 1,3,5-trimethyl-benzene / 3 h / Heating 7: 89 percent / Zr(acac)2, TBHP / CH2Cl2 8: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 9: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: 2.) 10percent HCl / 1.) Et2O, reflux, 4 h, 2.) CH2Cl2 2: 1.) N-methylmorpholine N-oxide, OsO4, 2.) sodium dithionite, 3.) 6N HCl / 1.) Me2CO, t-BuOH, 2 d, 2.) 1 h, 3.) CH2Cl2 3: 55 percent / Pd/C / 1,3,5-trimethyl-benzene / 3 h / Heating 4: 89 percent / Zr(acac)2, TBHP / CH2Cl2 5: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 6: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: Zn/HCl 2: CF3COOH, (CF3COO)2O 3: 2.) 10percent HCl / 1.) Et2O, reflux, 4 h, 2.) CH2Cl2 4: 1.) N-methylmorpholine N-oxide, OsO4, 2.) sodium dithionite, 3.) 6N HCl / 1.) Me2CO, t-BuOH, 2 d, 2.) 1 h, 3.) CH2Cl2 5: 55 percent / Pd/C / 1,3,5-trimethyl-benzene / 3 h / Heating 6: 89 percent / Zr(acac)2, TBHP / CH2Cl2 7: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 8: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: 1.) N-methylmorpholine N-oxide, OsO4, 2.) sodium dithionite, 3.) 6N HCl / 1.) Me2CO, t-BuOH, 2 d, 2.) 1 h, 3.) CH2Cl2 2: 55 percent / Pd/C / 1,3,5-trimethyl-benzene / 3 h / Heating 3: 89 percent / Zr(acac)2, TBHP / CH2Cl2 4: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 5: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: 55 percent / Pd/C / 1,3,5-trimethyl-benzene / 3 h / Heating 2: 89 percent / Zr(acac)2, TBHP / CH2Cl2 3: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 4: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: 89 percent / Zr(acac)2, TBHP / CH2Cl2 2: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 3: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: 98 percent / pyridine / CH2Cl2 / 18 h / 20 °C 2: 66 percent / CuCN, BF3*Et2O / tetrahydrofuran; diethyl ether / 8 h / -78 - 20 °C View Scheme

1: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 2: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme

1: 97.3 percent / polyphosphoric acid / 87 °C / 1) 1 min, 2) 30 min 2: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 3: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 4: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 5: 97 percent / p-TsOH monohydrate / benzene 6: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 7: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme