1.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 1.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 1.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 2.1: 90 percent / tetrahydrofuran / 2 h / sonication 3.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 4.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 5.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 6.1: 28 percent / propionic acid / 48 h / 180 °C 7.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 8.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 9.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 10.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 11.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 2.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 2.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 3.1: 90 percent / tetrahydrofuran / 2 h / sonication 4.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 5.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 6.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 7.1: 28 percent / propionic acid / 48 h / 180 °C 8.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 9.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 10.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 11.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 12.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: 95 percent / K2CO3 / acetone / 6 h / Heating 2.1: 90 percent / 24 h / 180 °C 3.1: 95 percent / KOH / methanol / 10 h / Heating 4.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 5.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 5.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 6.1: Mg; iodine / diethyl ether 6.2: 88 percent / diethyl ether / 3 h / 20 °C 7.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 8.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 8.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 8.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 9.1: 90 percent / tetrahydrofuran / 2 h / sonication 10.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 11.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 12.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 13.1: 28 percent / propionic acid / 48 h / 180 °C 14.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 15.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 16.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 17.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 18.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: Mg; iodine / diethyl ether 1.2: 88 percent / diethyl ether / 3 h / 20 °C 2.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 3.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 3.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 3.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 4.1: 90 percent / tetrahydrofuran / 2 h / sonication 5.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 6.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 7.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 8.1: 28 percent / propionic acid / 48 h / 180 °C 9.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 10.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 11.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 12.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 13.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: 95 percent / KOH / methanol / 10 h / Heating 2.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 3.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 3.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 4.1: Mg; iodine / diethyl ether 4.2: 88 percent / diethyl ether / 3 h / 20 °C 5.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 6.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 6.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 6.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 7.1: 90 percent / tetrahydrofuran / 2 h / sonication 8.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 9.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 10.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 11.1: 28 percent / propionic acid / 48 h / 180 °C 12.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 13.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 14.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 15.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 16.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: 90 percent / 24 h / 180 °C 2.1: 95 percent / KOH / methanol / 10 h / Heating 3.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 4.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 4.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 5.1: Mg; iodine / diethyl ether 5.2: 88 percent / diethyl ether / 3 h / 20 °C 6.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 7.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 7.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 7.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 8.1: 90 percent / tetrahydrofuran / 2 h / sonication 9.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 10.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 11.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 12.1: 28 percent / propionic acid / 48 h / 180 °C 13.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 14.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 15.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 16.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 17.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: 80 percent / zinc amalgam; HCl / ethanol / 3 h / Heating 2.1: 95 percent / K2CO3 / acetone / 6 h / Heating 3.1: 90 percent / 24 h / 180 °C 4.1: 95 percent / KOH / methanol / 10 h / Heating 5.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 6.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 6.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 7.1: Mg; iodine / diethyl ether 7.2: 88 percent / diethyl ether / 3 h / 20 °C 8.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 9.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 9.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 9.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 10.1: 90 percent / tetrahydrofuran / 2 h / sonication 11.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 12.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 13.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 14.1: 28 percent / propionic acid / 48 h / 180 °C 15.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 16.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 17.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 18.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 19.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1: With hydrazine monohydrochloride; hydrazine in diethylene glycol T=125°C; Huang-Minlon reduction; 2: With potassium hydroxide in diethylene glycol T=210°C;

Wilkinson's catalyst in benzene T=120 - 130°C; 20 h;

1: 90 percent / tetrahydrofuran / 2 h / sonication 2: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 3: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 4: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 5: 28 percent / propionic acid / 48 h / 180 °C 6: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 7: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 8: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 9: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 10: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme