1: LiNH2; NH3 2: H2 / Lindlar catalyst / ethanol / 0 °C 3: MnO2 / toluene 4: t-BuOK / tetrahydrofuran 5: p-TsOH / methanol 6: pyridine View Scheme

1: H2 / Lindlar catalyst / ethanol / 0 °C 2: MnO2 / toluene 3: t-BuOK / tetrahydrofuran 4: p-TsOH / methanol 5: pyridine View Scheme

1: 1.) MeLi / 1.) hexane, Et2O, a) -78 deg C, 2 h, b) -20 deg C, 15 min, 2.) hexane, Et2O, a) -78 deg C, 0.5 h, b) 25 deg C, 2 h 2: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 3: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 4: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 5: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C 6: pyridine / -10 °C View Scheme

1: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 2: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 3: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 4: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C 5: pyridine / -10 °C View Scheme

1: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 2: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C 3: pyridine / -10 °C View Scheme

1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 3: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C 4: pyridine / -10 °C View Scheme

1: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C 2: pyridine / -10 °C View Scheme

dilithium tetrachlorocuprate in tetrahydrofuran T=-20°C; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

pyridine T=-10°C;

1: MnO2 / toluene 2: t-BuOK / tetrahydrofuran 3: p-TsOH / methanol 4: pyridine View Scheme