1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 2: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 3: 84 percent / BnNMe3OH / methanol; tetrahydrofuran / 1 h / 0 °C 4: n-BuLi; WCl6 / tetrahydrofuran; hexane / 0 - 20 °C 5: 12 mg / pyridinum p-toluenesulfonate / methanol / 6 h / 0 °C 6: 69 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0 - 20 °C 7: 40 percent / aq. HF / acetonitrile / 0 - 20 °C View Scheme

1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 2: 84 percent / BnNMe3OH / methanol; tetrahydrofuran / 1 h / 0 °C 3: n-BuLi; WCl6 / tetrahydrofuran; hexane / 0 - 20 °C 4: 12 mg / pyridinum p-toluenesulfonate / methanol / 6 h / 0 °C 5: 69 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0 - 20 °C 6: 40 percent / aq. HF / acetonitrile / 0 - 20 °C View Scheme

1: 84 percent / BnNMe3OH / methanol; tetrahydrofuran / 1 h / 0 °C 2: n-BuLi; WCl6 / tetrahydrofuran; hexane / 0 - 20 °C 3: 12 mg / pyridinum p-toluenesulfonate / methanol / 6 h / 0 °C 4: 69 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0 - 20 °C 5: 40 percent / aq. HF / acetonitrile / 0 - 20 °C View Scheme

1.1: n-BuLi; LiCl; diisopropylamine / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 98 percent / hexane; tetrahydrofuran / 14 h / 0 - 20 °C 2.1: 77 percent / LiAlH4; EtOAc / hexane; tetrahydrofuran / 1.25 h / 0 °C 3.1: 63 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 20 °C 4.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 4.2: 60 percent / BF3*OEt2 / tetrahydrofuran; pentane / 3 h / -78 °C 5.1: 57 percent / second generation Grubbs catalyst / CH2Cl2 / 48 h / 50 - 55 °C 6.1: 89 percent / DMAP; 2,6-lutidine / pyridine / 1 h / 20 °C 7.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 8.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 9.1: 84 percent / BnNMe3OH / tetrahydrofuran; methanol / 1 h / 0 °C 10.1: n-BuLi; WCl6 / hexane; tetrahydrofuran / 0.67 h / 0 - 20 °C 11.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 0 °C 12.1: 69 percent / pyridine; Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 13.1: 40 percent / aq. HF / acetonitrile / 0.33 h / 20 °C View Scheme

1.1: 77 percent / LiAlH4; EtOAc / hexane; tetrahydrofuran / 1.25 h / 0 °C 2.1: 63 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 20 °C 3.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 3.2: 60 percent / BF3*OEt2 / tetrahydrofuran; pentane / 3 h / -78 °C 4.1: 57 percent / second generation Grubbs catalyst / CH2Cl2 / 48 h / 50 - 55 °C 5.1: 89 percent / DMAP; 2,6-lutidine / pyridine / 1 h / 20 °C 6.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 7.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 8.1: 84 percent / BnNMe3OH / tetrahydrofuran; methanol / 1 h / 0 °C 9.1: n-BuLi; WCl6 / hexane; tetrahydrofuran / 0.67 h / 0 - 20 °C 10.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 0 °C 11.1: 69 percent / pyridine; Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 12.1: 40 percent / aq. HF / acetonitrile / 0.33 h / 20 °C View Scheme

1.1: 85 percent / PPh3; I2; imidazole / acetonitrile; diethyl ether / 3 h / 20 °C 2.1: n-BuLi; LiCl; diisopropylamine / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 98 percent / hexane; tetrahydrofuran / 14 h / 0 - 20 °C 3.1: 77 percent / LiAlH4; EtOAc / hexane; tetrahydrofuran / 1.25 h / 0 °C 4.1: 63 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 20 °C 5.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 5.2: 60 percent / BF3*OEt2 / tetrahydrofuran; pentane / 3 h / -78 °C 6.1: 57 percent / second generation Grubbs catalyst / CH2Cl2 / 48 h / 50 - 55 °C 7.1: 89 percent / DMAP; 2,6-lutidine / pyridine / 1 h / 20 °C 8.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 9.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 10.1: 84 percent / BnNMe3OH / tetrahydrofuran; methanol / 1 h / 0 °C 11.1: n-BuLi; WCl6 / hexane; tetrahydrofuran / 0.67 h / 0 - 20 °C 12.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 0 °C 13.1: 69 percent / pyridine; Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 14.1: 40 percent / aq. HF / acetonitrile / 0.33 h / 20 °C View Scheme

1.1: 63 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 20 °C 2.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 2.2: 60 percent / BF3*OEt2 / tetrahydrofuran; pentane / 3 h / -78 °C 3.1: 57 percent / second generation Grubbs catalyst / CH2Cl2 / 48 h / 50 - 55 °C 4.1: 89 percent / DMAP; 2,6-lutidine / pyridine / 1 h / 20 °C 5.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 6.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 7.1: 84 percent / BnNMe3OH / tetrahydrofuran; methanol / 1 h / 0 °C 8.1: n-BuLi; WCl6 / hexane; tetrahydrofuran / 0.67 h / 0 - 20 °C 9.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 0 °C 10.1: 69 percent / pyridine; Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 11.1: 40 percent / aq. HF / acetonitrile / 0.33 h / 20 °C View Scheme

1.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 1.2: 60 percent / BF3*OEt2 / tetrahydrofuran; pentane / 3 h / -78 °C 2.1: 57 percent / second generation Grubbs catalyst / CH2Cl2 / 48 h / 50 - 55 °C 3.1: 89 percent / DMAP; 2,6-lutidine / pyridine / 1 h / 20 °C 4.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 5.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 6.1: 84 percent / BnNMe3OH / tetrahydrofuran; methanol / 1 h / 0 °C 7.1: n-BuLi; WCl6 / hexane; tetrahydrofuran / 0.67 h / 0 - 20 °C 8.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 0 °C 9.1: 69 percent / pyridine; Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 10.1: 40 percent / aq. HF / acetonitrile / 0.33 h / 20 °C View Scheme

1.1: 16.4 g / Zn; PPh3 / CH2Cl2 / 2 h 2.1: n-BuLi / tetrahydrofuran; hexane / 1.67 h / -78 - 23 °C 2.2: 100 percent / tetrahydrofuran; hexane / 8 h / 20 °C 3.1: 99.6 percent / TBAF / tetrahydrofuran / 5 h / 20 °C 4.1: Dess-Martin reagent / CH2Cl2 5.1: Sn(OTf); Et3N / CH2Cl2 / 1 h / -20 °C 5.2: 2.82 g / CH2Cl2 / 1 h / -78 °C 6.1: 75.0 mg / NaBH(OAc)3; AcOH / 3 h / 5 °C 7.1: 90 percent / DBU / CH2Cl2 / 2 h / 20 °C 8.1: tributyltin hydride; Pd(OAc)2; PCy3 / tetrahydrofuran; hexane 8.2: 769 mg / I2 / CH2Cl2 / 0.33 h 9.1: 433 mg / aq. K3PO4; PdCl2(dppf)*CH2Cl2 / diethyl ether; tetrahydrofuran; dimethylformamide / 18 h 10.1: DIBAL-H / toluene / 2 h / -78 °C 11.1: 361 mg / pyridine / 8 h / 20 °C 12.1: 91 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 13.1: 42 percent / SnCl4; molecular sieves 4A / CHCl3; CH2Cl2 / 14 h / -5 - 20 °C 14.1: 87 percent / NaOMe / methanol / 15 h / 25 °C 15.1: 98 percent / Et3N / CH2Cl2 16.1: 62 percent / IBX / dimethylformamide / 36 h 17.1: 50 percent / aq. HF / acetonitrile / 20 °C View Scheme

1.1: Sn(OTf); Et3N / CH2Cl2 / 1 h / -20 °C 1.2: 2.82 g / CH2Cl2 / 1 h / -78 °C 2.1: 75.0 mg / NaBH(OAc)3; AcOH / 3 h / 5 °C 3.1: 90 percent / DBU / CH2Cl2 / 2 h / 20 °C 4.1: tributyltin hydride; Pd(OAc)2; PCy3 / tetrahydrofuran; hexane 4.2: 769 mg / I2 / CH2Cl2 / 0.33 h 5.1: 433 mg / aq. K3PO4; PdCl2(dppf)*CH2Cl2 / diethyl ether; tetrahydrofuran; dimethylformamide / 18 h 6.1: DIBAL-H / toluene / 2 h / -78 °C 7.1: 361 mg / pyridine / 8 h / 20 °C 8.1: 91 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 9.1: 42 percent / SnCl4; molecular sieves 4A / CHCl3; CH2Cl2 / 14 h / -5 - 20 °C 10.1: 87 percent / NaOMe / methanol / 15 h / 25 °C 11.1: 98 percent / Et3N / CH2Cl2 12.1: 62 percent / IBX / dimethylformamide / 36 h 13.1: 50 percent / aq. HF / acetonitrile / 20 °C View Scheme