1: 84 percent / NaBH4 / ethanol / 0.42 h / 25 °C 2: triethylamine / 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / Ambient temperature 3: K2CO3 / methanol / 24 h / Ambient temperature 4: 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 5: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 6: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 7: 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 8: conc. HCl / methanol / 4.5 h / Heating 9: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: CH2Cl2 / 15 h / Ambient temperature 2: AlCl3, LiAlH4 / diethyl ether / 1.5 h / -15 - 0 °C View Scheme

1: NaBH4 / ethanol / 1 h / 0 °C 2: imidazole / dimethylformamide / 0 °C 3: K2CO3 / methanol / 1 h / 20 °C 4: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 5: tetrahydrofuran / 12 h / 0 - 20 °C 6: TBAF / tetrahydrofuran / 6 h View Scheme

1: 77 percent / PPTS / benzene / 3.5 h / Heating 2: dppf; N(Me)4Br / (Pd(π-allyl)Cl)2 / CH2Cl2; H2O / 2.5 h / 20 °C View Scheme

1: NaBH4 2: DMAP 3: K2CO3 / methanol 4: MnO2 / (COCl)2, DMSO and Et3N 5: 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 6: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating 7: PPTS / CH2Cl2 / 0.08 h / Ambient temperature 8: 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. 9: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C 10: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight 11: MeOH / PPTS / 0.08 h / Heating 12: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 13: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 14: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 15: PCC, sodium acetate / CH2Cl2 / 2.5 h 16: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 17: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 18: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: NaBH4 / ethanol / 1 h / 0 °C 2: imidazole / dimethylformamide / 0 °C 3: K2CO3 / methanol / 1 h / 20 °C 4: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 5: tetrahydrofuran / 12 h / 0 - 20 °C 6: TBAF / tetrahydrofuran / 6 h 7: Et3N / CH2Cl2 / 0 - 20 °C 8: 18-crown-6 / CH2Cl2 / 6 h / Heating View Scheme

1.1: NaBH4 / ethanol / 1 h / 0 °C 2.1: imidazole / dimethylformamide / 0 °C 3.1: K2CO3 / methanol / 1 h / 20 °C 4.1: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 5.1: tetrahydrofuran / 12 h / 0 - 20 °C 6.1: TBAF / tetrahydrofuran / 6 h 7.1: Et3N / CH2Cl2 / 0 - 20 °C 8.1: 18-crown-6 / CH2Cl2 / 6 h / Heating 9.1: diethyl ether / -78 - 0 °C 9.2: aq. NH4Cl / diethyl ether / 0.17 h / 0 °C View Scheme

1: NaBH4 2: DMAP 3: K2CO3 / methanol 4: MnO2 / (COCl)2, DMSO and Et3N 5: 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 6: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating 7: PPTS / CH2Cl2 / 0.08 h / Ambient temperature 8: 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. 9: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C 10: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight 11: MeOH / PPTS / 0.08 h / Heating 12: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 13: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 14: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 15: PCC, sodium acetate / CH2Cl2 / 2.5 h 16: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 17: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 18: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: 74 percent / diethyl ether / 3 h / 20 °C 2: 40 percent / O2; methylene blue / acetonitrile / Irradiation View Scheme

1: 87 percent / Jones reagent / acetone 2: conc. H2SO4 / Ambient temperature View Scheme