1: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 2: 88 percent / H2 / Lindlar / methanol 3: 1.) DMSO,(COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 4: (C6H11)2NMgBr / methanol / -55 °C 5: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

1: 1) (C6H11)2NMgBr / 1) THF, -55 deg C, 2) THF, -55 to -30 deg C, 1.2 h 2: 16 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature; phosphate buffer, pH = 6.86 View Scheme

1: 99 percent / DMSO, (COCl)2, Et3N / CH2Cl2 2: Ph3P / CH2Cl2 / -78 °C 3: LDA / tetrahydrofuran / -30 °C 4: n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 5: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 6: 88 percent / H2 / Lindlar / methanol 7: 1.) DMSO, (COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 8: 23 percent / (C6H11)2NMgBr / tetrahydrofuran / -55 °C 9: 95 percent / DDQ / CH2Cl2; H2O / 0.17 h / Ambient temperature 10: 70 percent / TFA, molecular sieves / CH2Cl2 View Scheme

1: n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 2: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 3: 88 percent / H2 / Lindlar / methanol 4: 1.) DMSO, (COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 5: 23 percent / (C6H11)2NMgBr / tetrahydrofuran / -55 °C 6: 95 percent / DDQ / CH2Cl2; H2O / 0.17 h / Ambient temperature 7: 70 percent / TFA, molecular sieves / CH2Cl2 View Scheme

1: Ph3P / CH2Cl2 / -78 °C 2: LDA / tetrahydrofuran / -30 °C 3: n-BuLi / 1.) THF, -78 deg C, 2.) oxidation 4: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 5: 88 percent / H2 / Lindlar / methanol 6: 1.) DMSO, (COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 7: 23 percent / (C6H11)2NMgBr / tetrahydrofuran / -55 °C 8: 95 percent / DDQ / CH2Cl2; H2O / 0.17 h / Ambient temperature 9: 70 percent / TFA, molecular sieves / CH2Cl2 View Scheme

1: 88 percent / H2 / Lindlar / methanol 2: 1.) DMSO, (COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 3: 23 percent / (C6H11)2NMgBr / tetrahydrofuran / -55 °C 4: 95 percent / DDQ / CH2Cl2; H2O / 0.17 h / Ambient temperature 5: 70 percent / TFA, molecular sieves / CH2Cl2 View Scheme

1: 1.) camphorsulfonic acid, 2.) n-Bu4NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C 2: 88 percent / H2 / Lindlar / methanol 3: 1.) DMSO, (COCl)2, Et3N, 2.) CSA / 1.) CH2Cl2, 2.) CH2Cl2, room temperature 4: 23 percent / (C6H11)2NMgBr / tetrahydrofuran / -55 °C 5: 95 percent / DDQ / CH2Cl2; H2O / 0.17 h / Ambient temperature 6: 70 percent / TFA, molecular sieves / CH2Cl2 View Scheme

1: 97 percent / BH3*SMe2 / diethyl ether 2: 96 percent / imidazole, DMAP / CH2Cl2 / 1 h / 0 °C 3: 90 percent / LiAlH4 / diethyl ether / 15 h / 0 °C 4: 91 percent / NaHCO3, NaCl / dimethylformamide / 1.) r.t., 30 min, 2.) r.t., 16 h 5: 87 percent / TBAF*3H2O / tetrahydrofuran / 12 h / Ambient temperature 6: 1.) oxalyl chloride, DMSO, 2.) N-methylmorpholine / 1.) CH2Cl2, -50 deg C, 2 min, 2.) CH2Cl2, -55 to 50 deg C, 20 min 7: 1.) tin(II) triflate, N-ethylpiperidine / 1.) CH2Cl2, -45 deg C, 3 h, 2.) CH2Cl2, -80 deg C, 20 min 8: 82 percent / NaBH4, H2O / tetrahydrofuran / 1.5 h 9: 94 percent / imidazole, DMAP / CH2Cl2 / 3 h / Ambient temperature 10: 93 percent / H2 / 5percent Pd/C / ethyl acetate / 15 h / Ambient temperature 11: N-methylmorpholine N-oxide / (Ph3P)3RuCl2 / acetone / 72 h / Ambient temperature 12: BuLi / diethyl ether / 1.) -30 deg C, 30 min, 2.) -50 to 0 deg C, 1 h 13: BF3*Et2O / 2 h / Ambient temperature 14: t-BuOK, 18-crown-6 / pentane / 2.5 h / Ambient temperature 15: BuLi / diethyl ether / 1.) -80 to -30 deg C, 1.5 h, 2.) -60 deg C to r.t., 5 h 16: H2SO4, H2O / tetrahydrofuran / 0.42 h / Ambient temperature 17: HF, I2, H2O / acetonitrile / 48 h / Ambient temperature 18: 82 percent / 2,6-lutidine / CH2Cl2 19: 14 percent / CeCl3*7H2O, NaBH4 / methanol / 1.67 h / -60 - 0 °C 20: DMAP, pyridine / CH2Cl2 / 12 h / Ambient temperature 21: pyridine*HF / tetrahydrofuran / 1 h / Ambient temperature 22: Dess-Martin periodinane / 0.67 h / Ambient temperature 23: tetrahydrofuran / 1 h / -80 - -47 °C 24: Dess-Martin periodinane / CH2Cl2 / 0.42 h / Ambient temperature 25: pyridine, CSA / CH2Cl2 / 1 h / Ambient temperature 26: 88 percent / K2CO3 / methanol / 60 h / Ambient temperature 27: 90 percent / 2,6-lutidine / CH2Cl2 28: 1.) dicyclohexylmagnesium bromide / 1.) THF, -65 to -50 deg C, 35 min, 2.) THF, -65 to -50 deg C, 40 min 29: 93 percent / TBAF / tetrahydrofuran / 34 h / Ambient temperature 30: 3 Angstroem molecular sieves, TFA / CH2Cl2 / 0.6 h / Ambient temperature View Scheme

1: 90 percent / LiAlH4 / diethyl ether / 15 h / 0 °C 2: 91 percent / NaHCO3, NaCl / dimethylformamide / 1.) r.t., 30 min, 2.) r.t., 16 h 3: 87 percent / TBAF*3H2O / tetrahydrofuran / 12 h / Ambient temperature 4: 1.) oxalyl chloride, DMSO, 2.) N-methylmorpholine / 1.) CH2Cl2, -50 deg C, 2 min, 2.) CH2Cl2, -55 to 50 deg C, 20 min 5: 1.) tin(II) triflate, N-ethylpiperidine / 1.) CH2Cl2, -45 deg C, 3 h, 2.) CH2Cl2, -80 deg C, 20 min 6: 82 percent / NaBH4, H2O / tetrahydrofuran / 1.5 h 7: 94 percent / imidazole, DMAP / CH2Cl2 / 3 h / Ambient temperature 8: 93 percent / H2 / 5percent Pd/C / ethyl acetate / 15 h / Ambient temperature 9: N-methylmorpholine N-oxide / (Ph3P)3RuCl2 / acetone / 72 h / Ambient temperature 10: BuLi / diethyl ether / 1.) -30 deg C, 30 min, 2.) -50 to 0 deg C, 1 h 11: BF3*Et2O / 2 h / Ambient temperature 12: t-BuOK, 18-crown-6 / pentane / 2.5 h / Ambient temperature 13: BuLi / diethyl ether / 1.) -80 to -30 deg C, 1.5 h, 2.) -60 deg C to r.t., 5 h 14: H2SO4, H2O / tetrahydrofuran / 0.42 h / Ambient temperature 15: HF, I2, H2O / acetonitrile / 48 h / Ambient temperature 16: 82 percent / 2,6-lutidine / CH2Cl2 17: 14 percent / CeCl3*7H2O, NaBH4 / methanol / 1.67 h / -60 - 0 °C 18: DMAP, pyridine / CH2Cl2 / 12 h / Ambient temperature 19: pyridine*HF / tetrahydrofuran / 1 h / Ambient temperature 20: Dess-Martin periodinane / 0.67 h / Ambient temperature 21: tetrahydrofuran / 1 h / -80 - -47 °C 22: Dess-Martin periodinane / CH2Cl2 / 0.42 h / Ambient temperature 23: pyridine, CSA / CH2Cl2 / 1 h / Ambient temperature 24: 88 percent / K2CO3 / methanol / 60 h / Ambient temperature 25: 90 percent / 2,6-lutidine / CH2Cl2 26: 1.) dicyclohexylmagnesium bromide / 1.) THF, -65 to -50 deg C, 35 min, 2.) THF, -65 to -50 deg C, 40 min 27: 93 percent / TBAF / tetrahydrofuran / 34 h / Ambient temperature 28: 3 Angstroem molecular sieves, TFA / CH2Cl2 / 0.6 h / Ambient temperature View Scheme

1: 96 percent / imidazole, DMAP / CH2Cl2 / 1 h / 0 °C 2: 90 percent / LiAlH4 / diethyl ether / 15 h / 0 °C 3: 91 percent / NaHCO3, NaCl / dimethylformamide / 1.) r.t., 30 min, 2.) r.t., 16 h 4: 87 percent / TBAF*3H2O / tetrahydrofuran / 12 h / Ambient temperature 5: 1.) oxalyl chloride, DMSO, 2.) N-methylmorpholine / 1.) CH2Cl2, -50 deg C, 2 min, 2.) CH2Cl2, -55 to 50 deg C, 20 min 6: 1.) tin(II) triflate, N-ethylpiperidine / 1.) CH2Cl2, -45 deg C, 3 h, 2.) CH2Cl2, -80 deg C, 20 min 7: 82 percent / NaBH4, H2O / tetrahydrofuran / 1.5 h 8: 94 percent / imidazole, DMAP / CH2Cl2 / 3 h / Ambient temperature 9: 93 percent / H2 / 5percent Pd/C / ethyl acetate / 15 h / Ambient temperature 10: N-methylmorpholine N-oxide / (Ph3P)3RuCl2 / acetone / 72 h / Ambient temperature 11: BuLi / diethyl ether / 1.) -30 deg C, 30 min, 2.) -50 to 0 deg C, 1 h 12: BF3*Et2O / 2 h / Ambient temperature 13: t-BuOK, 18-crown-6 / pentane / 2.5 h / Ambient temperature 14: BuLi / diethyl ether / 1.) -80 to -30 deg C, 1.5 h, 2.) -60 deg C to r.t., 5 h 15: H2SO4, H2O / tetrahydrofuran / 0.42 h / Ambient temperature 16: HF, I2, H2O / acetonitrile / 48 h / Ambient temperature 17: 82 percent / 2,6-lutidine / CH2Cl2 18: 14 percent / CeCl3*7H2O, NaBH4 / methanol / 1.67 h / -60 - 0 °C 19: DMAP, pyridine / CH2Cl2 / 12 h / Ambient temperature 20: pyridine*HF / tetrahydrofuran / 1 h / Ambient temperature 21: Dess-Martin periodinane / 0.67 h / Ambient temperature 22: tetrahydrofuran / 1 h / -80 - -47 °C 23: Dess-Martin periodinane / CH2Cl2 / 0.42 h / Ambient temperature 24: pyridine, CSA / CH2Cl2 / 1 h / Ambient temperature 25: 88 percent / K2CO3 / methanol / 60 h / Ambient temperature 26: 90 percent / 2,6-lutidine / CH2Cl2 27: 1.) dicyclohexylmagnesium bromide / 1.) THF, -65 to -50 deg C, 35 min, 2.) THF, -65 to -50 deg C, 40 min 28: 93 percent / TBAF / tetrahydrofuran / 34 h / Ambient temperature 29: 3 Angstroem molecular sieves, TFA / CH2Cl2 / 0.6 h / Ambient temperature View Scheme