2: 65 percent / triphenylphosphine / palladium acetate / tetrahydrofuran / 5 h / Heating 3: 95 percent / sodium hydride / diethyl ether / 0 °C 4: 70 percent / diethyl ether / -10 °C 5: 90 percent / triphenylphosphine, carbon tetrachloride / 12 h / Heating 6: diisobutylaluminium hydride / tetrahydrofuran / -40 °C 7: manganese dioxide / hexane / Ambient temperature 8: KCN, 18-crown-6 / 1 h / 0 °C 9: trimethylbenzylammonium fluoride / tetrahydrofuran; H2O / 0 °C 11: 79 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 56 °C 12: p-toluenesulfonic acid / methanol / 1 h / 0 °C 13: 2percent aqueous sodium hydroxide / diethyl ether / 0.33 h View Scheme

1.1: 85 percent / triphenylphosphine; N-bromosuccinimide / CH2Cl2 / 2 h / -20 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C 2.2: 81 percent / tetrahydrofuran; hexane / 3 h / -20 - 20 °C 3.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C 4.1: 95 percent / pyridine / CH2Cl2 / 48 h / -10 °C 5.1: perchloric acid / tetrahydrofuran; H2O / 2 h / Heating 5.2: 67 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C 6.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C 7.1: sodium iodide; 18-c-6 / butan-2-one / Heating 7.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating 8.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C 9.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 9.2: tetrahydrofuran; hexane / 0.5 h 10.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C 11.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C 12.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C 14.1: 4-dimethylaminopyridine / CH2Cl2 15.1: HCl / tetrahydrofuran / 5 h / 0 °C 16.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C 17.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating 18.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C 19.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 19.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 20.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 21.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 22.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 22.2: CH2Cl2 / 3 h / -78 - 20 °C 23.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 24.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 25.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1H-imidazole; iodine; triphenylphosphine in diethyl ether; acetonitrile T=0°C; 0.25 h; Yield given;

1: PBr3 / diethyl ether / 0.33 h / -25 °C 2: BuLi, N,N'-dimethyl-N,N'-propyleneurea / hexane; tetrahydrofuran / 1.) -78 deg C, 1 h; 2.) -50 deg C, 1 h 3: KOH / diethyl ether; methanol / 1 h / Ambient temperature 4: Na, dibenzo<18>crown-6 / liquid ammonia; tetrahydrofuran / 0.03 h View Scheme

1: PDC / CH2Cl2 / 10 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h 3: 94 percent / SOCl2, pyridine / benzene / 16 h / Ambient temperature 4: 91 percent / MeOK / toluene / 2 h / Ambient temperature 5: 1.) MeOK / 1.) cyclohexane, 38 deg C, 2 h View Scheme

1: PDC / CH2Cl2 / 10 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h 3: 94 percent / SOCl2, pyridine / benzene / 16 h / Ambient temperature 4: 91 percent / MeOK / toluene / 2 h / Ambient temperature 5: 1.) MeOK / 1.) cyclohexane, 38 deg C, 2 h View Scheme

1: 97 percent / aq. KOH / methanol / 0.08 h 2: 74 percent / H2 / PtO2 / methanol / 2 h 3: 100 percent / Jones reagent / acetone View Scheme

1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

1.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 23 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 23 °C / |Inert atmosphere 2.2: 24 h / 0 °C / |Inert atmosphere 3.1: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 4.1: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 5.1: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

1: 85 percent / Ph3P, N-chlorosuccinimide / tetrahydrofuran / 5 h / 20 °C 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h 3: 78 percent / Li, EtNH2 / tetrahydrofuran / 4 h / -78 °C 4: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 5: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 6: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 7: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 8: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C 9: 49 percent / SOCl2, pyridine / 3 h / 15 °C 10: 92 percent / MnO2 / hexane / 12 h / 15 °C 11: 65 percent / 67 percent aq. Ca(ClO)2, glacial acetic acid / acetonitrile / 20 h / 15 °C View Scheme