Li(1+)*C9H21S(1-) in N,N,N',N',N'',N''-hexamethylphosphoric triamide 3.5 h; Ambient temperature;

lithium n-propylmercaptide in N,N,N',N',N'',N''-hexamethylphosphoric triamide

1: 1.) (C6H11)2NMgBr / 1.) THF, -50 deg C, 2.) 0 deg C 2: 1.) NaOMe, 2.) Zn/AcOH, conc. HCl / 1.) CH2Cl2, MeOH, room temperature 2.) THF, room temperature 3: LiSPr / hexamethylphosphoric acid triamide / Ambient temperature View Scheme

1: BOP, Et3N / dimethylformamide / 18 h / 65 °C 2: PPTS, 4A sieves / 1,2-dichloro-ethane / 24 h / 80 °C 3: LiSPr / hexamethylphosphoric acid triamide / 3.5 h / Ambient temperature View Scheme

1: BOP, Et3N / dimethylformamide / 18 h / 65 °C 2: PPTS, 4A sieves / 1,2-dichloro-ethane / 24 h / 80 °C 3: LiSPr / hexamethylphosphoric acid triamide / 3.5 h / Ambient temperature View Scheme

1: CrO3, H2SO4 / acetone / 1 h / -20 - -5 °C 2: BOP, Et3N / dimethylformamide / 18 h / 65 °C 3: PPTS, 4A sieves / 1,2-dichloro-ethane / 24 h / 80 °C 4: LiSPr / hexamethylphosphoric acid triamide / 3.5 h / Ambient temperature View Scheme

1: TBAF / tetrahydrofuran / 2 h / Ambient temperature 2: CrO3, H2SO4 / acetone / 1 h / -20 - -5 °C 3: BOP, Et3N / dimethylformamide / 18 h / 65 °C 4: PPTS, 4A sieves / 1,2-dichloro-ethane / 24 h / 80 °C 5: LiSPr / hexamethylphosphoric acid triamide / 3.5 h / Ambient temperature View Scheme

1: CuSO4, TsOH 2: CrO3-2Pyr / CH2Cl2 / 0.5 h / 0 °C 3: tetrahydrofuran / -78 °C 4: pyridine 5: 1.) LDA, TBSCl, HMPA, 2.) Bu4NF / 1.) THF, -78 deg C, 2.) reflux, 1.5 h 7: 95 percent / p-toluenesulfonic acid / 0 °C 8: i-Pr2NEt / CH2Cl2 9: lithium aluminum hydride / diethyl ether 10: CH2Cl2 11: 1.) butyllithium, 2.) Hg(OAc)2 / 1.) heptane, 2.) THF, water 12: CrO3-2Pyr / CH2Cl2 / 0 °C 13: tetrahydrofuran / -78 °C 14: DDQ / dioxane / 10 h 15: Bu4NF / tetrahydrofuran 16: CrO3-2Pyr / CH2Cl2 / 0 °C 17: 2.) camphorsulphonic acid / 1.) THF, -100 deg C, 2.) methylene chloride, -15 deg C, 10 h 18: 1.) Cr2(OAc)4-2H2O, 2.) potassium carbonate, methanol / 1.) EtOH, 2.) water View Scheme

1: CrO3-2Pyr / CH2Cl2 / 0.5 h / 0 °C 2: tetrahydrofuran / -78 °C 3: pyridine 4: 1.) LDA, TBSCl, HMPA, 2.) Bu4NF / 1.) THF, -78 deg C, 2.) reflux, 1.5 h 6: 95 percent / p-toluenesulfonic acid / 0 °C 7: i-Pr2NEt / CH2Cl2 8: lithium aluminum hydride / diethyl ether 9: CH2Cl2 10: 1.) butyllithium, 2.) Hg(OAc)2 / 1.) heptane, 2.) THF, water 11: CrO3-2Pyr / CH2Cl2 / 0 °C 12: tetrahydrofuran / -78 °C 13: DDQ / dioxane / 10 h 14: Bu4NF / tetrahydrofuran 15: CrO3-2Pyr / CH2Cl2 / 0 °C 16: 2.) camphorsulphonic acid / 1.) THF, -100 deg C, 2.) methylene chloride, -15 deg C, 10 h 17: 1.) Cr2(OAc)4-2H2O, 2.) potassium carbonate, methanol / 1.) EtOH, 2.) water View Scheme

1: tetrahydrofuran / -78 °C 2: pyridine 3: 1.) LDA, TBSCl, HMPA, 2.) Bu4NF / 1.) THF, -78 deg C, 2.) reflux, 1.5 h 5: 95 percent / p-toluenesulfonic acid / 0 °C 6: i-Pr2NEt / CH2Cl2 7: lithium aluminum hydride / diethyl ether 8: CH2Cl2 9: 1.) butyllithium, 2.) Hg(OAc)2 / 1.) heptane, 2.) THF, water 10: CrO3-2Pyr / CH2Cl2 / 0 °C 11: tetrahydrofuran / -78 °C 12: DDQ / dioxane / 10 h 13: Bu4NF / tetrahydrofuran 14: CrO3-2Pyr / CH2Cl2 / 0 °C 15: 2.) camphorsulphonic acid / 1.) THF, -100 deg C, 2.) methylene chloride, -15 deg C, 10 h 16: 1.) Cr2(OAc)4-2H2O, 2.) potassium carbonate, methanol / 1.) EtOH, 2.) water View Scheme