1: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 2: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 3: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 2: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: K2CO3, 18-crown-6 / toluene / Ambient temperature 2: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 3: PCC, sodium acetate / CH2Cl2 / 2.5 h 4: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 5: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 6: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: MeOH / PPTS / 0.08 h / Heating 2: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 3: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 4: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 5: PCC, sodium acetate / CH2Cl2 / 2.5 h 6: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 7: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 8: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: O3 2: NaBH4 / ethanol 3: DMAP, Et3N 4: K2CO3, MeOH 5: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C 6: 78 percent / n-BuLi, TMEDA, triisopropoxy chloro titanium (IV) <ClTi(O-i-Pr)3> / diethyl ether / -78 - -10 °C 7: 84 percent / LiAlH4 / tetrahydrofuran / Heating 8: ppts / CH2Cl2 9: 1.) (Siam)2BH; 2.) H2O2, NaOH 10: 90 percent / Ph3P, I2, imidazole / acetonitrile; tetrahydrofuran / -10 °C 11: 85 percent / NaH / dimethylsulfoxide 12: ppts / methanol / Heating 13: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C 14: NaH / 1,2-dimethoxy-ethane; various solvent(s) 15: 10percent HCl 16: PCC, NaOAc, Celite / CH2Cl2 17: 75 percent / LDA 18: 1-cyclohexyl-3-(2-N-methylmorpholinoethyl)carbodiimide p-toluenesulfonate / CuCl2 / acetonitrile / 60 °C 19: 84 percent / KOH / ethanol; H2O / Heating View Scheme

1: 1.) DMSO, (COCl)2 2.) Et3N 2: K2CO3, 18-crown-6 / toluene / Ambient temperature 3: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 4: PCC, sodium acetate / CH2Cl2 / 2.5 h 5: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 6: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 7: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: MeOH, PPTS 2: 1.) DMSO, (COCl)2 2.) Et3N 3: K2CO3, 18-crown-6 / toluene / Ambient temperature 4: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 5: PCC, sodium acetate / CH2Cl2 / 2.5 h 6: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 7: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 8: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme