(i) O2, rose bengal, NaOAc, MeOH, (UV-irradiation), (ii) aq. HCl, THF; Multistep reaction;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 70 percent / tetrahydrofuran; hexane / -78 - 0 °C 2.1: 67 percent / PCC; silica gel / CH2Cl2 / 4 h / 25 °C 3.1: 70 percent / n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 4.1: 93 percent / NaBH4; CeCl3*7H2O / ethanol / 1 h / 0 °C 5.1: n-Bu3SnH; AIBN / toluene / 2.5 h / 80 °C 5.2: 71 percent / I2 / CH2Cl2 / 0.17 h / 25 °C 6.1: AsPh3 / Pd2(dba)3 / 1-methyl-pyrrolidin-2-one / 0.17 h 6.2: 67 percent / 1-methyl-pyrrolidin-2-one / 3 h / 30 °C 7.1: Dess-Martin periodinane; pyridne / CH2Cl2 / 1.5 h / 25 °C View Scheme

1: 87 percent / dimsyl sodium / tetrahydrofuran; dimethylsulfoxide / 1 h / 0 °C 2: 80 percent / MgBr2 / diethyl ether / 0.75 h / Ambient temperature View Scheme

1: 87 percent / dimsyl sodium / tetrahydrofuran; dimethylsulfoxide / 1 h / 0 °C 2: 80 percent / MgBr2 / diethyl ether / 0.75 h / Ambient temperature 3: 4 g / KOH / methanol / 0.67 h / Ambient temperature View Scheme

1: 88 percent / tetrahydrofuran / Heating 2: 54 percent / P2O5; Celite / toluene / Heating 3: 78 percent / KOH 4: ethanol; H2O / 45 °C / pH 3.0 View Scheme

(i) nBuLi, hexane, THF, (ii) /BRN= 2205868/, (iii) aq. HCO2H; Multistep reaction;

hydrogen; palladium on activated charcoal

diisobutylaluminium hydride in hexane; dichloromethane T=-78°C; Inert atmosphere;

1: 47 percent / LDA, HMPT 2: 75 percent / pentane / 6 h / Irradiation View Scheme

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -70 °C 1.2: cerium(III) chloride / tetrahydrofuran / 2 h / -70 °C 1.3: tetrahydrofuran / 2 h / -70 °C 2.1: sodium hydroxide / methanol; H2O / 4 h / 25 °C 3.1: sodium hydrogen carbonate; iodine / diethyl ether; H2O / 25 °C 4.1: pyridine; thionyl chloride / 1 h / 60 °C 5.1: tri-n-butyltin hydride; 1,1-azobis(cyclohexanecarbonitrile) View Scheme