1.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 2.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 3.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 4.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 4.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 5.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 6.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 7.1: toluene / 12 h / Heating 8.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 9.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 10.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 11.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 12.1: CH2Cl2 / 0.17 h / 20 °C 12.2: 97 percent / K2CO3 / methanol / 1.25 h 13.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 1.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 2.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 4.1: toluene / 12 h / Heating 5.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 6.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 7.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 8.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 9.1: CH2Cl2 / 0.17 h / 20 °C 9.2: 97 percent / K2CO3 / methanol / 1.25 h 10.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 2.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 3.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 3.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 4.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 5.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 6.1: toluene / 12 h / Heating 7.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 8.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 9.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 10.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 11.1: CH2Cl2 / 0.17 h / 20 °C 11.2: 97 percent / K2CO3 / methanol / 1.25 h 12.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: toluene / 12 h / Heating 2.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 3.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 4.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 5.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 6.1: CH2Cl2 / 0.17 h / 20 °C 6.2: 97 percent / K2CO3 / methanol / 1.25 h 7.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 2.1: toluene / 12 h / Heating 3.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 4.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 5.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 6.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 7.1: CH2Cl2 / 0.17 h / 20 °C 7.2: 97 percent / K2CO3 / methanol / 1.25 h 8.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 3.1: toluene / 12 h / Heating 4.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 5.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 6.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 7.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 8.1: CH2Cl2 / 0.17 h / 20 °C 8.2: 97 percent / K2CO3 / methanol / 1.25 h 9.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1: HCl / methanol / 0.5 h / Ambient temperature 2: LiOH / tetrahydrofuran; methanol; H2O / 24 h / Ambient temperature 3: N-ethyldiisopropylamine, bis(2-oxo-3-oxazolidinyl)phosphic chloride / toluene / 15 h / 85 °C 4: 100 percent / TBAF / tetrahydrofuran / 44 h / Ambient temperature 5: 91 percent / trifluoroacetic acid / CH2Cl2 / 17 h / Ambient temperature 6: 100 percent / AgO, 1 M aq. HNO3 / dioxane / 2.5 h / Ambient temperature View Scheme

1: Dess-Martin periodinane / CH2Cl2 / 2 h / 25 °C 2: 85 percent / sec-BuLi / tetrahydrofuran / 4.5 h / -78 - 20 °C 3: 76 percent / BF3*Et2O / 2 h / -78 - -20 °C 4: imidazole / dimethylformamide / 16 h / 40 °C 5: DDQ, H2O / CH2Cl2 / 1 h / 25 °C 6: Swern oxidation 7: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 5 h 8: NaH / dimethylformamide / 6.5 h / 0 °C 9: OsO4, NaIO4 / tetrahydrofuran / 17 h / 25 °C / phosphate buffer pH 7 10: KN(SiMe3)2, 18-crown-6 / tetrahydrofuran / 4 h / -78 °C 11: DIBAL / toluene / 1 h / -78 °C 12: PDC / CH2Cl2 / 24 h / 25 °C 13: CH2Cl2 / 22 h / 40 °C 14: 1.) 0.02percent aq. HCl, 2.) aq. LiOH / 1.) MeOH, 25 deg C, 0.5 h, 2.) THF, MeOH, 25 deg C , 29 h 15: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr2NEt / toluene / 15 h / 85 °C 16: n-Bu4NF / tetrahydrofuran / 48 h / 25 °C 17: TFA / CH2Cl2 / 17 h / 25 °C 18: AgO, 1M HNO3 / dioxane / 2.5 h / 25 °C View Scheme

1: 85 percent / sec-BuLi / tetrahydrofuran / 4.5 h / -78 - 20 °C 2: 76 percent / BF3*Et2O / 2 h / -78 - -20 °C 3: imidazole / dimethylformamide / 16 h / 40 °C 4: DDQ, H2O / CH2Cl2 / 1 h / 25 °C 5: Swern oxidation 6: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 5 h 7: NaH / dimethylformamide / 6.5 h / 0 °C 8: OsO4, NaIO4 / tetrahydrofuran / 17 h / 25 °C / phosphate buffer pH 7 9: KN(SiMe3)2, 18-crown-6 / tetrahydrofuran / 4 h / -78 °C 10: DIBAL / toluene / 1 h / -78 °C 11: PDC / CH2Cl2 / 24 h / 25 °C 12: CH2Cl2 / 22 h / 40 °C 13: 1.) 0.02percent aq. HCl, 2.) aq. LiOH / 1.) MeOH, 25 deg C, 0.5 h, 2.) THF, MeOH, 25 deg C , 29 h 14: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr2NEt / toluene / 15 h / 85 °C 15: n-Bu4NF / tetrahydrofuran / 48 h / 25 °C 16: TFA / CH2Cl2 / 17 h / 25 °C 17: AgO, 1M HNO3 / dioxane / 2.5 h / 25 °C View Scheme

1: 76 percent / BF3*Et2O / 2 h / -78 - -20 °C 2: imidazole / dimethylformamide / 16 h / 40 °C 3: DDQ, H2O / CH2Cl2 / 1 h / 25 °C 4: Swern oxidation 5: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 5 h 6: NaH / dimethylformamide / 6.5 h / 0 °C 7: OsO4, NaIO4 / tetrahydrofuran / 17 h / 25 °C / phosphate buffer pH 7 8: KN(SiMe3)2, 18-crown-6 / tetrahydrofuran / 4 h / -78 °C 9: DIBAL / toluene / 1 h / -78 °C 10: PDC / CH2Cl2 / 24 h / 25 °C 11: CH2Cl2 / 22 h / 40 °C 12: 1.) 0.02percent aq. HCl, 2.) aq. LiOH / 1.) MeOH, 25 deg C, 0.5 h, 2.) THF, MeOH, 25 deg C , 29 h 13: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr2NEt / toluene / 15 h / 85 °C 14: n-Bu4NF / tetrahydrofuran / 48 h / 25 °C 15: TFA / CH2Cl2 / 17 h / 25 °C 16: AgO, 1M HNO3 / dioxane / 2.5 h / 25 °C View Scheme