1: 75 percent / pyridine; CH2Cl2 / Ambient temperature 2: 100 percent / dimethylsulfoxide / 80 - 85 °C 3: 76 percent / K2CO3 / methanol / Ambient temperature 4: 100 percent / imidazole / dimethylformamide / Ambient temperature 5: DIBAH / CH2Cl2 / -78 °C 6: NaBH4 / methanol / Ambient temperature 7: 90 percent / n-Bu4NF / tetrahydrofuran / Ambient temperature View Scheme

1: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature 2: K2CO3 / methanol / 24 h / Ambient temperature 3: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 4: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 5: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 6: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 7: conc. HCl / methanol / 4.5 h / Heating 8: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: imidazole / dimethylformamide / 0 °C 2: K2CO3 / methanol / 1 h / 20 °C 3: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 4: tetrahydrofuran / 12 h / 0 - 20 °C 5: TBAF / tetrahydrofuran / 6 h View Scheme

1: DMAP 2: K2CO3 / methanol 3: MnO2 / (COCl)2, DMSO and Et3N 4: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h 5: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating 6: PPTS / CH2Cl2 / 0.08 h / Ambient temperature 7: 1.) B2H6, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H2O2 / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min. 8: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C 9: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight 10: MeOH / PPTS / 0.08 h / Heating 11: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 12: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 13: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 14: PCC, sodium acetate / CH2Cl2 / 2.5 h 15: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 16: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 17: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: imidazole / dimethylformamide / 0 °C 2: K2CO3 / methanol / 1 h / 20 °C 3: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 4: tetrahydrofuran / 12 h / 0 - 20 °C 5: TBAF / tetrahydrofuran / 6 h 6: Et3N / CH2Cl2 / 0 - 20 °C 7: 18-crown-6 / CH2Cl2 / 6 h / Heating View Scheme

1.1: imidazole / dimethylformamide / 0 °C 2.1: K2CO3 / methanol / 1 h / 20 °C 3.1: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 4.1: tetrahydrofuran / 12 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 6 h 6.1: Et3N / CH2Cl2 / 0 - 20 °C 7.1: 18-crown-6 / CH2Cl2 / 6 h / Heating 8.1: diethyl ether / -78 - 0 °C 8.2: aq. NH4Cl / diethyl ether / 0.17 h / 0 °C View Scheme

1: DMAP 2: K2CO3 / methanol 3: MnO2 / (COCl)2, DMSO and Et3N 4: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h 5: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating 6: PPTS / CH2Cl2 / 0.08 h / Ambient temperature 7: 1.) B2H6, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H2O2 / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min. 8: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C 9: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight 10: MeOH / PPTS / 0.08 h / Heating 11: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 12: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 13: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 14: PCC, sodium acetate / CH2Cl2 / 2.5 h 15: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 16: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 17: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1.1: pyridine / CH2Cl2 / 7 h / 20 °C 2.1: 26.6 g / NaI / acetone / 24 h / 20 °C 3.1: 92 percent / KHCO3 / methanol / 2 h 4.1: 93 percent / imidazole / dimethylformamide / 1 h / 0 °C 5.1: 96 percent / benzene / 8 h / Heating 6.1: KH; 18-crown-6 / -78 °C 6.2: 83 percent / tetrahydrofuran / 16 h / -78 - -60 °C 7.1: aq. AcOH / tetrahydrofuran / 0.08 h / 20 °C 8.1: 55 mg / NaBH4 / ethanol / 0.5 h / 0 °C 9.1: 93 percent / p-TsOH*H2O / methanol / 0.25 h / 20 °C View Scheme

Multi-step reaction with 2 steps 1: 100 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 4 h / 20 °C2: 100 percent / K2CO3 / methanol / 1 h / 0 °C  

Multi-step reaction with 3 steps 1: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature2: K2CO3 / methanol / 24 h / Ambient temperature3: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h