1: NaOH / methanol / 2 h / Ambient temperature 2: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 3: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 4: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

Multi-step reaction with 9 steps 1: 72 percent / benzene / 16 h / Heating2: 88 percent / H2 / Pd/C / ethyl acetate4: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature5: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature6: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C7: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C8: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C9: toluene / 5 h / 90 °C  

Multi-step reaction with 8 steps 1: 88 percent / H2 / Pd/C / ethyl acetate3: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature4: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature5: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C6: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C7: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C8: toluene / 5 h / 90 °C  

Multi-step reaction with 11 steps 1: 91 percent / Na / ethanol / 0.25 h2: DMSO, oxalyl chloride, Et3N / CH2Cl2 / 0.75 h / -78 °C3: 72 percent / benzene / 16 h / Heating4: 88 percent / H2 / Pd/C / ethyl acetate6: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature7: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature8: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C9: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C10: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C11: toluene / 5 h / 90 °C  

Multi-step reaction with 7 steps 2: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature3: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature4: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C5: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C6: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C7: toluene / 5 h / 90 °C