1.1: TMSOTf 2.1: OsO4; NMO 3.1: Pb(OAc)4; K2CO3 4.1: 78 percent / toluene 5.1: 80 percent / DIBAL-H / tetrahydrofuran 6.1: 91 percent / DMSO; oxalyl chloride 7.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 8.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 9.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 10.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 11.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 11.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 12.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 13.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 14.1: toluene / 12 h / Heating 15.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 16.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 17.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 18.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 19.1: CH2Cl2 / 0.17 h / 20 °C 19.2: 97 percent / K2CO3 / methanol / 1.25 h 20.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 78 percent / toluene 2.1: 80 percent / DIBAL-H / tetrahydrofuran 3.1: 91 percent / DMSO; oxalyl chloride 4.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 5.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 6.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 7.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 8.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 8.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 9.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 10.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 11.1: toluene / 12 h / Heating 12.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 13.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 14.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 15.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 16.1: CH2Cl2 / 0.17 h / 20 °C 16.2: 97 percent / K2CO3 / methanol / 1.25 h 17.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 98 percent / TBAF 2.1: BCl3*SMe2 2.2: NaIO4 3.1: TMSOTf 4.1: OsO4; NMO 5.1: Pb(OAc)4; K2CO3 6.1: 78 percent / toluene 7.1: 80 percent / DIBAL-H / tetrahydrofuran 8.1: 91 percent / DMSO; oxalyl chloride 9.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 10.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 11.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 12.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 13.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 13.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 14.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 15.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 16.1: toluene / 12 h / Heating 17.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 18.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 19.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 20.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 21.1: CH2Cl2 / 0.17 h / 20 °C 21.2: 97 percent / K2CO3 / methanol / 1.25 h 22.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 91 percent / DMSO; oxalyl chloride 2.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 3.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 4.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 5.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 6.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 6.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 8.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 9.1: toluene / 12 h / Heating 10.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 11.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 12.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 13.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 14.1: CH2Cl2 / 0.17 h / 20 °C 14.2: 97 percent / K2CO3 / methanol / 1.25 h 15.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 2.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 3.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 4.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 5.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 5.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 6.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 7.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 8.1: toluene / 12 h / Heating 9.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 10.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 11.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 12.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 13.1: CH2Cl2 / 0.17 h / 20 °C 13.2: 97 percent / K2CO3 / methanol / 1.25 h 14.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: BCl3*SMe2 1.2: NaIO4 2.1: TMSOTf 3.1: OsO4; NMO 4.1: Pb(OAc)4; K2CO3 5.1: 78 percent / toluene 6.1: 80 percent / DIBAL-H / tetrahydrofuran 7.1: 91 percent / DMSO; oxalyl chloride 8.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 9.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 10.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 11.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 12.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 12.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 13.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 14.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 15.1: toluene / 12 h / Heating 16.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 17.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 18.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 19.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 20.1: CH2Cl2 / 0.17 h / 20 °C 20.2: 97 percent / K2CO3 / methanol / 1.25 h 21.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 80 percent / DIBAL-H / tetrahydrofuran 2.1: 91 percent / DMSO; oxalyl chloride 3.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 4.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 5.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 6.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 7.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 7.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 8.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 9.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 10.1: toluene / 12 h / Heating 11.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 12.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 13.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 14.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 15.1: CH2Cl2 / 0.17 h / 20 °C 15.2: 97 percent / K2CO3 / methanol / 1.25 h 16.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 98 percent / TBAF 2.1: BCl3*SMe2 2.2: NaIO4 3.1: TMSOTf 4.1: OsO4; NMO 5.1: Pb(OAc)4; K2CO3 6.1: 78 percent / toluene 7.1: 80 percent / DIBAL-H / tetrahydrofuran 8.1: 91 percent / DMSO; oxalyl chloride 9.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 10.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 11.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 12.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 13.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 13.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 14.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 15.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 16.1: toluene / 12 h / Heating 17.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 18.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 19.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 20.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 21.1: CH2Cl2 / 0.17 h / 20 °C 21.2: 97 percent / K2CO3 / methanol / 1.25 h 22.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 98 percent / TBAF 2.1: BCl3*SMe2 2.2: NaIO4 3.1: TMSOTf 4.1: OsO4; NMO 5.1: Pb(OAc)4; K2CO3 6.1: 78 percent / toluene 7.1: 80 percent / DIBAL-H / tetrahydrofuran 8.1: 91 percent / DMSO; oxalyl chloride 9.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 10.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 11.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 12.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 13.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 13.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 14.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 15.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 16.1: toluene / 12 h / Heating 17.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 18.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 19.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 20.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 21.1: CH2Cl2 / 0.17 h / 20 °C 21.2: 97 percent / K2CO3 / methanol / 1.25 h 22.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: OsO4; NMO 2.1: Pb(OAc)4; K2CO3 3.1: 78 percent / toluene 4.1: 80 percent / DIBAL-H / tetrahydrofuran 5.1: 91 percent / DMSO; oxalyl chloride 6.1: 77 percent / boron trifluoride etherate / tetrahydrofuran; cyclohexane / -78 - -5 °C 7.1: 97 percent / imidazole / dimethylformamide / 0 - 20 °C 8.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h / 20 °C 9.1: 145 mg / K2CO3; Pb(OAc)4 / benzene / 5.5 h / 20 °C 10.1: 18-crown-6-ether; KN(TMS)2 / toluene; tetrahydrofuran / 0.08 h / -78 °C 10.2: 208 mg / tetrahydrofuran; toluene / 3 h / -78 °C 11.1: 92 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 12.1: 97 percent / DMSO; oxalyl chloride / CH2Cl2 / 0.5 h / -78 °C 13.1: toluene / 12 h / Heating 14.1: 83 percent / NaBH4; sulfur / tetrahydrofuran / 5 h / Heating 15.1: LiOH; H2O / methanol; tetrahydrofuran / 48 h / 20 °C 16.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 17.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 18.1: CH2Cl2 / 0.17 h / 20 °C 18.2: 97 percent / K2CO3 / methanol / 1.25 h 19.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme