potassium dihydrogenphosphate; Fremy’s salt in acetone 0.5 h; Ambient temperature;

1: 95 percent / ImH / dimethylformamide / 12 h / 60 °C 2: NBS, AIBN / CCl4 / 2 h / 77 °C / Irradiation 3: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 4: Bu4NF / tetrahydrofuran / 7 h / 0 °C 5: MeI / acetonitrile / 1.5 h / 80 °C 6: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 7: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 8: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 9: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: NBS, AIBN / CCl4 / 2 h / 77 °C / Irradiation 2: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 3: Bu4NF / tetrahydrofuran / 7 h / 0 °C 4: MeI / acetonitrile / 1.5 h / 80 °C 5: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 6: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 7: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 8: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide (BMPS) / 3 h / 350 °C / 40 Torr 2: NaBH4 / methanol / -78 °C 3: NaH / dimethylformamide / 2 h / 25 °C 4: 1.) BH3, 2.) pyridinium chlorochromate (PCC) / 1.) THF, 24 deg C, 4 h, 2.) CH2Cl2, 1.5 h 5: tetrahydrofuran / 2 h / 0 - 24 °C 6: hexamethylphosphoric acid triamide / 1 h / 210 °C 7: 1.) BH3 / 1.) THF, 15 deg C, 12 h, 2.) PhMe, 12 atm, 6 h 8: tetrahydrofuran / 3 h / -10 °C 9: SiO2 10: oxone / tetrahydrofuran; H2O / 6 h / 0 °C 11: ethanol / 12 h / 68 °C 12: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 13: Bu4NF / tetrahydrofuran / 7 h / 0 °C 14: MeI / acetonitrile / 1.5 h / 80 °C 15: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 16: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 17: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 18: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: NaBH4 / methanol / -78 °C 2: NaH / dimethylformamide / 2 h / 25 °C 3: 1.) BH3, 2.) pyridinium chlorochromate (PCC) / 1.) THF, 24 deg C, 4 h, 2.) CH2Cl2, 1.5 h 4: tetrahydrofuran / 2 h / 0 - 24 °C 5: hexamethylphosphoric acid triamide / 1 h / 210 °C 6: 1.) BH3 / 1.) THF, 15 deg C, 12 h, 2.) PhMe, 12 atm, 6 h 7: tetrahydrofuran / 3 h / -10 °C 8: SiO2 9: oxone / tetrahydrofuran; H2O / 6 h / 0 °C 10: ethanol / 12 h / 68 °C 11: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 12: Bu4NF / tetrahydrofuran / 7 h / 0 °C 13: MeI / acetonitrile / 1.5 h / 80 °C 14: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 15: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 16: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 17: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: 1.) BH3 / 1.) THF, 15 deg C, 12 h, 2.) PhMe, 12 atm, 6 h 2: tetrahydrofuran / 3 h / -10 °C 3: SiO2 4: oxone / tetrahydrofuran; H2O / 6 h / 0 °C 5: ethanol / 12 h / 68 °C 6: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 7: Bu4NF / tetrahydrofuran / 7 h / 0 °C 8: MeI / acetonitrile / 1.5 h / 80 °C 9: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 10: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 11: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 12: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 2: Bu4NF / tetrahydrofuran / 7 h / 0 °C 3: MeI / acetonitrile / 1.5 h / 80 °C 4: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 5: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 6: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 7: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: tetrahydrofuran / 3 h / -10 °C 2: SiO2 3: oxone / tetrahydrofuran; H2O / 6 h / 0 °C 4: ethanol / 12 h / 68 °C 5: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 6: Bu4NF / tetrahydrofuran / 7 h / 0 °C 7: MeI / acetonitrile / 1.5 h / 80 °C 8: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 9: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 10: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 11: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: oxone / tetrahydrofuran; H2O / 6 h / 0 °C 2: ethanol / 12 h / 68 °C 3: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 4: Bu4NF / tetrahydrofuran / 7 h / 0 °C 5: MeI / acetonitrile / 1.5 h / 80 °C 6: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 7: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 8: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 9: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme

1: NaH / dimethylformamide / 2 h / 25 °C 2: 1.) BH3, 2.) pyridinium chlorochromate (PCC) / 1.) THF, 24 deg C, 4 h, 2.) CH2Cl2, 1.5 h 3: tetrahydrofuran / 2 h / 0 - 24 °C 4: hexamethylphosphoric acid triamide / 1 h / 210 °C 5: 1.) BH3 / 1.) THF, 15 deg C, 12 h, 2.) PhMe, 12 atm, 6 h 6: tetrahydrofuran / 3 h / -10 °C 7: SiO2 8: oxone / tetrahydrofuran; H2O / 6 h / 0 °C 9: ethanol / 12 h / 68 °C 10: LDA / tetrahydrofuran / 2 h / 0 - 24 °C 11: Bu4NF / tetrahydrofuran / 7 h / 0 °C 12: MeI / acetonitrile / 1.5 h / 80 °C 13: aq. CuCl2 / tetrahydrofuran / 4 h / 23 °C 14: 2.) AcOH / 1.) THF, from -78 to 0 deg C, 12 h 15: H2 / Pd/C / ethyl acetate / 6 h / 23 °C / 2068.6 Torr 16: 69 percent / aq. NO(KSO3)2, KH2PO4 / acetone / 2 h / 23 °C View Scheme