1.1: Zn(OTf)2; Et3N; (+)-N-methylephedrine / toluene / 18 h / 20 °C 2.1: 4.44 g / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 3.1: 85 percent / K2CO3; 18-crown-6 / toluene / 26 h / Heating 4.1: 93 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 5.1: 56 percent / EtMgBr; i-PrOH / CH2Cl2 / 39 h / 0 - 20 °C 6.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 7.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 8.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 9.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 10.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 11.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 12.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 13.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 14.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 15.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 16.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 17.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 18.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 19.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 20.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 21.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 22.1: 2,4,6-trichlorobenzoyl chloride; Et3N 22.2: 74 percent / 4-dimethylaminopyridine 23.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 24.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 56 percent / EtMgBr; i-PrOH / CH2Cl2 / 39 h / 0 - 20 °C 2.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 3.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 4.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 5.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 6.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 7.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 8.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 9.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 10.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 11.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 12.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 13.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 14.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 15.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 16.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 17.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 18.1: 2,4,6-trichlorobenzoyl chloride; Et3N 18.2: 74 percent / 4-dimethylaminopyridine 19.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 20.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: nBuLi / diethyl ether; various solvent(s) / 0.17 h / -40 °C 1.2: 85 percent / diethyl ether / 12 h / -18 °C 2.1: 76 percent / EtMgBr; i-PrOH / CH2Cl2 / 18 h / 20 °C 3.1: 90 percent / diisopropylethylamine / CH2Cl2 / 0.42 h / 0 °C 4.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 4.2: 87 percent / tetrahydrofuran / -78 - 20 °C 5.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 6.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 7.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 8.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 9.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 10.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 11.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 12.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 13.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 14.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 15.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 16.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 17.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 18.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 19.1: 2,4,6-trichlorobenzoyl chloride; Et3N 19.2: 74 percent / 4-dimethylaminopyridine 20.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 21.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 90 percent / diisopropylethylamine / CH2Cl2 / 0.42 h / 0 °C 2.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 2.2: 87 percent / tetrahydrofuran / -78 - 20 °C 3.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 4.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 5.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 6.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 7.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 8.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 9.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 10.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 11.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 12.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 13.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 14.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 15.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 16.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 17.1: 2,4,6-trichlorobenzoyl chloride; Et3N 17.2: 74 percent / 4-dimethylaminopyridine 18.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 19.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 93 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 2.1: 56 percent / EtMgBr; i-PrOH / CH2Cl2 / 39 h / 0 - 20 °C 3.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 4.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 5.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 6.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 7.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 8.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 9.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 10.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 11.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 12.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 13.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 14.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 15.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 16.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 17.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 18.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 19.1: 2,4,6-trichlorobenzoyl chloride; Et3N 19.2: 74 percent / 4-dimethylaminopyridine 20.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 21.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 85 percent / K2CO3; 18-crown-6 / toluene / 26 h / Heating 2.1: 93 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 3.1: 56 percent / EtMgBr; i-PrOH / CH2Cl2 / 39 h / 0 - 20 °C 4.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 5.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 6.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 7.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 8.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 9.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 10.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 11.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 12.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 13.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 14.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 15.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 16.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 17.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 18.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 19.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 20.1: 2,4,6-trichlorobenzoyl chloride; Et3N 20.2: 74 percent / 4-dimethylaminopyridine 21.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 22.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 1.2: 87 percent / tetrahydrofuran / -78 - 20 °C 2.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 3.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 4.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 5.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 6.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 7.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 8.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 9.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 10.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 11.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 12.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 13.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 14.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 15.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 16.1: 2,4,6-trichlorobenzoyl chloride; Et3N 16.2: 74 percent / 4-dimethylaminopyridine 17.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 18.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 2.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 3.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 4.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 5.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 6.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 7.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 8.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 9.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 10.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 11.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 12.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 13.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 14.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 15.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 16.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 17.1: 2,4,6-trichlorobenzoyl chloride; Et3N 17.2: 74 percent / 4-dimethylaminopyridine 18.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 19.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 2.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 3.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 4.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 5.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 6.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 7.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 8.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 9.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 10.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 11.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 12.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 13.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 14.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 15.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 16.1: 2,4,6-trichlorobenzoyl chloride; Et3N 16.2: 74 percent / 4-dimethylaminopyridine 17.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 18.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: O3 / CH2Cl2 / 0.03 h / -78 °C 1.2: 83 percent / PPh3 / CH2Cl2 / 4 h / 20 °C 2.1: Zn(OTf)2; Et3N; (+)-N-methylephedrine / toluene / 18 h / 20 °C 3.1: 4.44 g / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 4.1: 85 percent / K2CO3; 18-crown-6 / toluene / 26 h / Heating 5.1: 93 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 6.1: 56 percent / EtMgBr; i-PrOH / CH2Cl2 / 39 h / 0 - 20 °C 7.1: 87 percent / diethylisopropylamine / CH2Cl2 / 0.42 h / 0 °C 8.1: 80 percent / DBU; LiCl / acetonitrile / 20 °C 9.1: SmI2 / tetrahydrofuran / 0.25 h / 0 °C 10.1: 146 mg / B(OH)3; H2O / tetrahydrofuran / 0.5 h / 20 °C 11.1: 90 percent / NaBH4; Et3B / methanol; tetrahydrofuran / 6 h / -78 °C 12.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 13.1: 122 mg / Bu4NF*3H2O / tetrahydrofuran / 2 h / Heating 14.1: 75 percent / Et3N; DMAP / CH2Cl2 / 7.5 h / 0 - 20 °C 15.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 16.1: 101 mg / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 / 0.33 h / 20 °C 17.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 18.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 19.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 20.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 21.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 22.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 23.1: 2,4,6-trichlorobenzoyl chloride; Et3N 23.2: 74 percent / 4-dimethylaminopyridine 24.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 25.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme