1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C 2: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h 3: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 4: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 5: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h 2: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 3: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 4: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1.1: BF3*OEt2; Ph3SiH / CH2Cl2 / 2.5 h / -78 - 20 °C 1.2: DIBAL-H / toluene / 3 h / -78 °C 1.3: 826 mg / Cs2CO3 / toluene; propan-2-ol / 17 h / 20 °C 2.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C 3.1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h 4.1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 5.1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 6.1: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1: 9 percent / second generation Grubbs catalyst / CH2Cl2 / 80 °C 2: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C 3: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h 4: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 5: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 6: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O 2: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN 3: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C 2: tetrahydrofuran 3: 76 percent / TiCl4 / CH2Cl2 / -78 °C 4: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O 5: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN 6: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 76 percent / TiCl4 / CH2Cl2 / -78 °C 2: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O 3: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN 4: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C 2: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 3: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C 2: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C View Scheme

1: LiN(SiMe3)2 / tetrahydrofuran / -40 °C 2: 95 percent / K2CO3 / CH2Cl2 / Heating 3: AlCl3 / 1,2-dichloro-ethane / -10 °C 4: 65 percent / LiBr, Li2CO3 / dimethylformamide / 150 °C 5: HCl*Et2O / ethanol / 50 °C View Scheme