1: 87 percent / NaH / dimethylformamide 2: 70 percent / BCl3 / -78 °C 3: 80 percent / camphorsulfonic acid monohydrate 4: 90 percent / (Ph3P)2PdCl2; Et3N / N,N-dimethyl-acetamide / 100 °C 5: camphorsulfonic acid monohydrate / tetrahydrofuran 6: NaBH4 / methanol 7: Pb(OAc)4 / benzene 8: NaBH4 / methanol 9: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating 10: (PhO)2P(O)N3; Ph3P; diethyl azodicarboxylate / tetrahydrofuran 11: 100 percent / H2 / 10 percent Pd/C / ethanol 12: methanol / 110 °C 13: NaBH(OAc)3 / methanol 14: 98 percent / Na; NH3 / tetrahydrofuran 15: 60 percent / AcOH / Heating View Scheme