1: diisobutylaluminum hydride (DIBAL) / CH2Cl2; hexane / 0.5 h / -78 °C 2: 1.) lithium diisopropylamide (LDA) / 1.) THF, 0 deg C, 10 min, 2.) THF, hexane, 0 deg C, 1 h 3: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min 4: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min 5: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C 6: 99 percent / K2CO3 / tetrahydrofuran; toluene 7: 85 percent / MeI, H2O / acetonitrile / Ambient temperature 8: 1.) t-BuLi, 2.) dineopentylzinc 9: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 10: benzene; diethyl ether / 0.33 h 11: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 12: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 13: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 14: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 15: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 16: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 17: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: sodium / ethanol / 2 h / Heating 2: H2O, NaCl / dimethylsulfoxide / 6 h / 145 - 180 °C 3: methanesulfonic acid, formic acid / 6 h / Heating View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: 55 percent / NaNO₂, HCl<br />2: 57 percent / BH₃*S(CH₃)2 / tetrahydrofuran<br />3: 58 percent / CBr₄, PPh₃ / acetonitrile<br /> <br /> &nbsp;