1: Br2; Et3N / CH2Cl2 2: 510 mg / DBU / benzene / 20 °C 3: 55 percent / (MeCN)2PdCl2; AsPh3 / 1-methyl-pyrrolidin-2-one / 1.5 h / 80 °C 4: 98 percent / TBAF; AcOH / tetrahydrofuran 5: 88 percent / H2 / [Ir(COD)(py)PCy3]PF6 / CH2Cl2 / 3 h / 51714.8 Torr 6: 88 percent / diphenylphosphorylazide; DBU / tetrahydrofuran / 0 - 20 °C 7: H2 / Pd/C / ethanol / 1 h 8: K2CO3 / acetonitrile / 2 h / Heating 9: 10 mg / LiAlH(OMe)3 / tetrahydrofuran / 40 h / Heating View Scheme

1: Br2, Et3N / CH2Cl2 / 0 °C 2: DBU / benzene 3: 55 percent / (MeCN)2PdCl2, AsPh3, NMP / 1.5 h / 80 °C 4: 100 percent / TBAF, AcOH / tetrahydrofuran / 72 h 5: 88 percent / H2, <Ir(COD)pyCy3>PF6 / CH2Cl2 / 51714.8 Torr 6: 100 percent / activated MnO2 / CHCl3 View Scheme

1: Br2, Et3N / CH2Cl2 / 0 °C 2: DBU / benzene 3: 55 percent / (MeCN)2PdCl2, AsPh3, NMP / 1.5 h / 80 °C 4: 100 percent / TBAF, AcOH / tetrahydrofuran / 72 h 5: 88 percent / H2, <Ir(COD)pyCy3>PF6 / CH2Cl2 / 51714.8 Torr 6: 100 percent / activated MnO2 / CHCl3 View Scheme