1.1: 84 percent / NaIO4; OsO4; H2O / tetrahydrofuran 2.1: DIBAL-H; BHT / toluene 3.1: pyridine 4.1: (i-Pr)MgCl / tetrahydrofuran / -10 °C 5.1: DBU / CH2Cl2 6.1: n-butyllitium / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C 6.2: 73 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 4 h / -78 °C 7.1: (EtO)3SiH / Cp*Ru(CH3CN)3PF6 / CH2Cl2 / 3 h / 20 °C 7.2: 92 percent / cesium fluoride; ethanol / CH2Cl2 / 12 h / 20 °C 8.1: pyridine / CH2Cl2 9.1: DIBAL-H / tetrahydrofuran / -78 °C 10.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C 10.2: 1,2-dimethoxy-ethane / -78 - 20 °C 11.1: CAN; H2O / acetone 12.1: aq. NaOH / tetrahydrofuran; methanol 13.1: 61 percent / MsCl; Et3N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating 14.1: 77 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C 1.2: 1,2-dimethoxy-ethane / -78 - 20 °C 2.1: CAN; H2O / acetone 3.1: aq. NaOH / tetrahydrofuran; methanol 4.1: 61 percent / MsCl; Et3N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating 5.1: 77 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: (i-Pr)MgCl / tetrahydrofuran / -10 °C 2.1: DBU / CH2Cl2 3.1: n-butyllitium / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C 3.2: 73 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 4 h / -78 °C 4.1: (EtO)3SiH / Cp*Ru(CH3CN)3PF6 / CH2Cl2 / 3 h / 20 °C 4.2: 92 percent / cesium fluoride; ethanol / CH2Cl2 / 12 h / 20 °C 5.1: pyridine / CH2Cl2 6.1: DIBAL-H / tetrahydrofuran / -78 °C 7.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C 7.2: 1,2-dimethoxy-ethane / -78 - 20 °C 8.1: CAN; H2O / acetone 9.1: aq. NaOH / tetrahydrofuran; methanol 10.1: 61 percent / MsCl; Et3N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating 11.1: 77 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: pyridine / CH2Cl2 2.1: DIBAL-H / tetrahydrofuran / -78 °C 3.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C 3.2: 1,2-dimethoxy-ethane / -78 - 20 °C 4.1: CAN; H2O / acetone 5.1: aq. NaOH / tetrahydrofuran; methanol 6.1: 61 percent / MsCl; Et3N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating 7.1: 77 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C 1.2: 1,2-dimethoxy-ethane / -78 - 20 °C 2.1: CAN; H2O / acetone 3.1: aq. NaOH / tetrahydrofuran; methanol 4.1: 61 percent / MsCl; Et3N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating 5.1: 77 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

1.1: DIBAL-H / tetrahydrofuran / -78 °C 2.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C 2.2: 1,2-dimethoxy-ethane / -78 - 20 °C 3.1: CAN; H2O / acetone 4.1: aq. NaOH / tetrahydrofuran; methanol 5.1: 61 percent / MsCl; Et3N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating 6.1: 77 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

ammonium cerium (IV) nitrate; water in acetonitrile T=0 - 20°C;

L-Selectridereg; in tetrahydrofuran T=-78°C; Reduction; 2.5 h;

1.1: 95.1 percent / mCPBA 2.1: 46.4 percent / (R,R)-salenCo(III)OAc / H2O / 72 h / 10 - 20 °C 3.1: 99 percent / H2 / Pd/C; Co(OAc)4 / methanol / 20 °C / 760 Torr 4.1: TMSOTf / CH2Cl2; petroleum ether / 2 h 5.1: 2.70 g / NaOMe / methanol / 3 h / 20 °C 6.1: 73.3 percent / DMAP; Et3N / CH2Cl2 / 20 °C 7.1: 86.1 percent / dimethylsulfoxide / 20 °C 8.1: 72.4 percent / cateholborane / 36 h / 20 °C 9.1: 95.4 percent / I2; aq. NaOH / diethyl ether / 0.33 h / 20 °C 10.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 10.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 10.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 11.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 12.1: 96.4 percent / diethyl ether / 1 h / 0 °C 13.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 14.1: MnO2 / CH2Cl2 / 3 h / Heating 15.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 16.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 16.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 17.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme

1.1: 99 percent / H2 / Pd/C; Co(OAc)4 / methanol / 20 °C / 760 Torr 2.1: TMSOTf / CH2Cl2; petroleum ether / 2 h 3.1: 2.70 g / NaOMe / methanol / 3 h / 20 °C 4.1: 73.3 percent / DMAP; Et3N / CH2Cl2 / 20 °C 5.1: 86.1 percent / dimethylsulfoxide / 20 °C 6.1: 72.4 percent / cateholborane / 36 h / 20 °C 7.1: 95.4 percent / I2; aq. NaOH / diethyl ether / 0.33 h / 20 °C 8.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 8.2: MeCuCNLi / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 8.3: 92.6 percent / tetrahydrofuran; hexane; diethyl ether / 1 h / -78 °C 9.1: 131 mg / (S)-2-methyl-CBS-oxazaborolidine; BH3*Me2S / tetrahydrofuran; toluene / 0.25 h / 0 °C 10.1: 96.4 percent / diethyl ether / 1 h / 0 °C 11.1: 72 percent / Li-naphthalene / tetrahydrofuran / -25 °C 12.1: MnO2 / CH2Cl2 / 3 h / Heating 13.1: 33.6 mg / NaH2PO4; 2-methyl-2-butene; NaClO2 / 2-methyl-propan-2-ol; H2O / 20 °C 14.1: NEt3; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 6 h 14.2: 81 percent / DMAP / tetrahydrofuran; toluene / Heating 15.1: 91 percent / aq. HCl / tetrahydrofuran; H2O / 48 h / 20 °C View Scheme