1.1: TsOH*H2O / methanol / 4 h / 50 °C 2.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C 3.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 3.2: diethyl ether / 12 h / -20 - 20 °C 3.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 4.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 5.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 6.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 7.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 8.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 9.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 9.2: NH4Br / various solvents / 2 h / 20 °C 9.3: 89 percent / NaBH4 / various solvents / 20 °C 10.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 10.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation 11.1: BBr3 View Scheme

1.1: 92 percent / DIBAL-H / toluene / -78 °C 2.1: 97 percent / 2,6-lutidine / CH2Cl2 / 20 °C 3.1: Pd(OAc)2; 1,2-bis(dicyclohexylphosphino)ethane / N,N-dimethyl-acetamide / 80 °C 3.2: TBAF / tetrahydrofuran / 20 °C 4.1: 97 percent / MnO2 / acetone / 20 °C 5.1: NaCNBH3 / methanol / Heating 6.1: Et3N / CH2Cl2 / 20 °C 7.1: 93 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 20 °C 8.1: NaN(TMS)2 / tetrahydrofuran / 0 °C 9.1: TFA / CH2Cl2 / 20 °C 10.1: NaCNBH3; 4 Angstroem molecular sieves / methanol / 0 °C 11.1: TsOH / CH2Cl2 / 20 °C 11.2: dimethyldioxirane / CH2Cl2 / 20 °C 11.3: 45 percent / DBU / CH2Cl2 / 20 °C 12.1: 98 percent / NaBH4 / ethanol / 80 °C 13.1: NaIO4 / tetrahydrofuran; H2O / 20 °C 13.2: 64 percent / CH2Cl2 / 70 °C 14.1: 50 percent / Ph3SiOReO3; TsOH / benzene / 60 °C View Scheme

1.1: TsOH*H2O / methanol / 4 h / 50 °C 2.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C 3.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 3.2: diethyl ether / 12 h / -20 - 20 °C 3.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 4.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 5.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 6.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 7.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 8.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 9.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 9.2: NH4Br / various solvents / 2 h / 20 °C 9.3: 89 percent / NaBH4 / various solvents / 20 °C 10.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 10.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation View Scheme

palladium diacetate; (iPr)NEt; triphenylphosphine in acetonitrile T=100°C;