1: 92 percent / Me3Al / toluene / 20 °C 2: 87 percent / NaH / dimethylformamide 3: 70 percent / BCl3 / -78 °C 4: 80 percent / camphorsulfonic acid monohydrate 5: 90 percent / (Ph3P)2PdCl2; Et3N / N,N-dimethyl-acetamide / 100 °C 6: camphorsulfonic acid monohydrate / tetrahydrofuran 7: NaBH4 / methanol 8: Pb(OAc)4 / benzene 9: NaBH4 / methanol 10: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating 11: (PhO)2P(O)N3; Ph3P; diethyl azodicarboxylate / tetrahydrofuran 12: 100 percent / H2 / 10 percent Pd/C / ethanol 13: methanol / 110 °C 14: NaBH(OAc)3 / methanol 15: 98 percent / Na; NH3 / tetrahydrofuran 16: 60 percent / AcOH / Heating View Scheme

1: NaBH4 / methanol 2: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating 3: (PhO)2P(O)N3; Ph3P; diethyl azodicarboxylate / tetrahydrofuran 4: 100 percent / H2 / 10 percent Pd/C / ethanol 5: methanol / 110 °C 6: NaBH(OAc)3 / methanol 7: 98 percent / Na; NH3 / tetrahydrofuran 8: 60 percent / AcOH / Heating View Scheme

1: (PhO)2P(O)N3; Ph3P; diethyl azodicarboxylate / tetrahydrofuran 2: 100 percent / H2 / 10 percent Pd/C / ethanol 3: methanol / 110 °C 4: NaBH(OAc)3 / methanol 5: 98 percent / Na; NH3 / tetrahydrofuran 6: 60 percent / AcOH / Heating View Scheme

1: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating 2: (PhO)2P(O)N3; Ph3P; diethyl azodicarboxylate / tetrahydrofuran 3: 100 percent / H2 / 10 percent Pd/C / ethanol 4: methanol / 110 °C 5: NaBH(OAc)3 / methanol 6: 98 percent / Na; NH3 / tetrahydrofuran 7: 60 percent / AcOH / Heating View Scheme

1: 100 percent / H2 / 10 percent Pd/C / ethanol 2: methanol / 110 °C 3: NaBH(OAc)3 / methanol 4: 98 percent / Na; NH3 / tetrahydrofuran 5: 60 percent / AcOH / Heating View Scheme

1: camphorsulfonic acid monohydrate / tetrahydrofuran 2: NaBH4 / methanol 3: Pb(OAc)4 / benzene 4: NaBH4 / methanol 5: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating 6: (PhO)2P(O)N3; Ph3P; diethyl azodicarboxylate / tetrahydrofuran 7: 100 percent / H2 / 10 percent Pd/C / ethanol 8: methanol / 110 °C 9: NaBH(OAc)3 / methanol 10: 98 percent / Na; NH3 / tetrahydrofuran 11: 60 percent / AcOH / Heating View Scheme

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

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

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

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