1: 1) n-BuLi / 1a) THF, hexane, -30 deg C, 15 min, 1b) THF, hexane, 0 deg C, 15 min, 2) THF, hexane, 58 to 60 deg C, 20 h 2: conc. H2SO4 / methanol / 16 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / 0 °C 4: NaN3 / dimethylsulfoxide / Ambient temperature 5: 1) PPh3, 2) H2O / 1) THF, 16 h, rt, 2) THF, 5 h, rt View Scheme

2: 95 percent / sodium bismethoxyethoxyaluminum hydride (Red-Al) / diethyl ether / 1.) 0 deg C, 1 h; 2.) room temp., 12 h 3: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 0 °C 4: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5: Dowex AG 50 W acidic ion exchange resin / methanol / 3 h / 40 °C 6: Et3N / CH2Cl2 / 1 h / 0 °C 7: LiBr / tetrahydrofuran / 18 h / Heating View Scheme

2: 95 percent / sodium bismethoxyethoxyaluminum hydride (Red-Al) / diethyl ether / 1.) 0 deg C, 1 h; 2.) room temp., 12 h 3: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 0 °C 4: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5: Dowex AG 50 W acidic ion exchange resin / methanol / 3 h / 40 °C 6: Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

1.1: n-butyllithium; HMPA / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 3.1: water; Hg(OTf)2 / acetonitrile / 0.17 h / 20 °C / Inert atmosphere View Scheme

1: ethyl magnesium bromide; benzene / und anschliessend mit wss. Schwefelsaeure 2: acetone; chromium (VI)-oxide; aqueous sulfuric acid View Scheme

1.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 °C 2.1: 9.95 g / p-TsOH / methanol; H2O / 1 h / 20 °C 3.1: 91 percent / I2; imidazole; PPh3 / toluene / 2 h / 20 °C 4.1: 99 percent / acetonitrile / 16 h / Heating 5.1: KN(SiMe3)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C 5.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C 6.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 7.1: KOH / H2O; methanol / 60 °C 8.1: 2.12 g / TsOH / CH2Cl2 / 0.5 h / 20 °C 9.1: 68 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 8 h / 20 °C 10.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 11.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 12.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 13.1: 81 percent / pyridine / 3 h / Heating 14.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 15.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 16.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 17.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 18.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 19.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 20.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 20.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 21.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 22.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

indium trifluoromethanesulfonate in methanol; water T=0 - 20°C; 10 h;

1: n-butyllithium; N,N,N',N',N'',N''-hexamethylphosphoric triamide / tetrahydrofuran / -78 - 20 °C 2: Jone's reagent / acetone / 0 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / 2.5 h / -78 °C 1.2: 99 percent / tetrahydrofuran / -35 - 20 °C 2.1: 99 percent / 4-methylbenzenesulfonic acid / methanol / 20 °C View Scheme

pyridinium p-toluenesulfonate in dichloromethane 4.5 h; Ambient temperature;