1.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 1.2: diethyl ether / 12 h / -20 - 20 °C 1.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 2.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 3.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 4.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 5.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 6.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 7.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 7.2: NH4Br / various solvents / 2 h / 20 °C 7.3: 89 percent / NaBH4 / various solvents / 20 °C 8.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 8.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation 9.1: BBr3 View Scheme

1: triphenylphosphine; diisopropyl azodicarboxylate / diethyl ether 2: p-toluenesolfonic acid; water / tetrahydrofuran 3: 91 percent / Pd(OAc)2; bis(diphenylphosphanyl)propane; Ag2CO3 / toluene / 24 h / 107 °C 4: 57 percent / SeO2; NaH2PO4 / dioxane / 3 h / 150 °C 5: methanol 6: diisobutylaluminum hydride 7: sodium cyanoborohydride / H2O View Scheme

1.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 1.2: diethyl ether / 12 h / -20 - 20 °C 1.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 2.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 3.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 4.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 5.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 6.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 7.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 7.2: NH4Br / various solvents / 2 h / 20 °C 7.3: 89 percent / NaBH4 / various solvents / 20 °C 8.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 8.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation View Scheme