1.1: 88 percent / triphenylphosphine; carbon tetrabromide; pyridine / benzene / 0.5 h / 50 °C 2.1: 100 percent / aq. HCl / acetone / 0.5 h / 20 °C 3.1: 100 percent / SmI2; methanol / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C 4.1: TBAF; 2,6-di-t-butyl-4-hydroxytoluene / tetrahydrofuran / 3 h / 20 °C 4.2: 45 percent / sodium methoxide / methanol; tetrahydrofuran / 60 h / 20 °C 5.1: pyridine / CH2Cl2 / 0.25 h / 20 °C 6.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C 7.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C 8.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 9.1: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 0.08 h / 20 °C 10.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C 10.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 11.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C 12.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C 13.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH2Cl2 / 0.05 h / 20 °C 14.1: 80 percent / lithium diisopropyl amide; MoO5*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C 15.1: 92 percent / DMAP / CH2Cl2 / 0.5 h / 20 °C 16.1: 68 percent / DBN / toluene / 10 h / Heating 17.1: 86 percent / OsO4; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C 18.1: 86 percent / DBU / toluene / 4 h / Heating 19.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C 20.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C 21.1: 97 percent / H2 / Pd(OH)2 / ethanol / 1 h / 20 °C 22.1: 94 percent / pyridine / CH2Cl2 / 1 h / -78 - 0 °C 23.1: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 24.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 25.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 26.1: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 27.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 28.1: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 29.1: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme

1: 96 percent / 4-methylmorpholine N-oxide. 4A molecular sieves, tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 25 °C 2: 93 percent Turnov. / aq. K2CO3 / methanol / 2.5 h / 0 °C 3: 85 percent / pyridine / toluene / 0.5 h / 0 °C 4: 95 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h / 25 °C 5: tetrahydrofuran; cyclohexane / 15 h / -78 °C 6: 94 percent Turnov. / NaBH4 / methanol / 3 h / 25 °C 7: 86 percent Turnov. / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 0 °C 8: 80 percent / HF*pyridine / tetrahydrofuran / 1.25 h / 25 °C View Scheme

1: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating 2: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 3: 95 percent / CH2Cl2 / 15 h / -45 °C 4: 63 percent / Burgess' reagent 5: 100 percent / pyridine 6: 65 percent / OsO4 7: DBU / toluene / 2 h / 105 °C 8: 75 percent / pyridine, DMAP / 24 h / 25 °C 9: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 10: tetrahydrofuran / 0.17 h / -78 °C 11: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 12: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 13: pyridine, DMAP / 20 h / 25 °C 14: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 15: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 16: HF, pyridine / acetonitrile / 1 h / 0 °C 17: H2 / Pd/C / ethanol / 1 h View Scheme

1: O3 2: KMnO4, KH2PO4 4: 93 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 5: 100 percent / p-TsOH 6: 92 percent / PhSK / dimethylformamide / 3 h / 86 °C 7: acid 8: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating 9: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 10: 95 percent / CH2Cl2 / 15 h / -45 °C 11: 63 percent / Burgess' reagent 12: 100 percent / pyridine 13: 65 percent / OsO4 14: DBU / toluene / 2 h / 105 °C 15: 75 percent / pyridine, DMAP / 24 h / 25 °C 16: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 17: tetrahydrofuran / 0.17 h / -78 °C 18: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 19: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 20: pyridine, DMAP / 20 h / 25 °C 21: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 22: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 23: HF, pyridine / acetonitrile / 1 h / 0 °C 24: H2 / Pd/C / ethanol / 1 h View Scheme

1: KMnO4, KH2PO4 3: 93 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 4: 100 percent / p-TsOH 5: 92 percent / PhSK / dimethylformamide / 3 h / 86 °C 6: acid 7: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating 8: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 9: 95 percent / CH2Cl2 / 15 h / -45 °C 10: 63 percent / Burgess' reagent 11: 100 percent / pyridine 12: 65 percent / OsO4 13: DBU / toluene / 2 h / 105 °C 14: 75 percent / pyridine, DMAP / 24 h / 25 °C 15: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 16: tetrahydrofuran / 0.17 h / -78 °C 17: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 18: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 19: pyridine, DMAP / 20 h / 25 °C 20: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 21: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 22: HF, pyridine / acetonitrile / 1 h / 0 °C 23: H2 / Pd/C / ethanol / 1 h View Scheme

1: acid 2: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating 3: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 4: 95 percent / CH2Cl2 / 15 h / -45 °C 5: 63 percent / Burgess' reagent 6: 100 percent / pyridine 7: 65 percent / OsO4 8: DBU / toluene / 2 h / 105 °C 9: 75 percent / pyridine, DMAP / 24 h / 25 °C 10: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 11: tetrahydrofuran / 0.17 h / -78 °C 12: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 13: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 14: pyridine, DMAP / 20 h / 25 °C 15: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 16: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 17: HF, pyridine / acetonitrile / 1 h / 0 °C 18: H2 / Pd/C / ethanol / 1 h View Scheme

1: 100 percent / p-TsOH 2: 92 percent / PhSK / dimethylformamide / 3 h / 86 °C 3: acid 4: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating 5: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 6: 95 percent / CH2Cl2 / 15 h / -45 °C 7: 63 percent / Burgess' reagent 8: 100 percent / pyridine 9: 65 percent / OsO4 10: DBU / toluene / 2 h / 105 °C 11: 75 percent / pyridine, DMAP / 24 h / 25 °C 12: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 13: tetrahydrofuran / 0.17 h / -78 °C 14: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 15: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 16: pyridine, DMAP / 20 h / 25 °C 17: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 18: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 19: HF, pyridine / acetonitrile / 1 h / 0 °C 20: H2 / Pd/C / ethanol / 1 h View Scheme

1: 93 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C 2: 100 percent / p-TsOH 3: 92 percent / PhSK / dimethylformamide / 3 h / 86 °C 4: acid 5: 92 percent / EtN(i-Pr)2, (Bu)4NI / CH2Cl2 / 32 h / Heating 6: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 7: 95 percent / CH2Cl2 / 15 h / -45 °C 8: 63 percent / Burgess' reagent 9: 100 percent / pyridine 10: 65 percent / OsO4 11: DBU / toluene / 2 h / 105 °C 12: 75 percent / pyridine, DMAP / 24 h / 25 °C 13: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 14: tetrahydrofuran / 0.17 h / -78 °C 15: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 16: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 17: pyridine, DMAP / 20 h / 25 °C 18: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 19: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 20: HF, pyridine / acetonitrile / 1 h / 0 °C 21: H2 / Pd/C / ethanol / 1 h View Scheme

1: 1.) LDA, 2.) mCPBA / 1.) THF, -78 deg C, 2.) hexane, 25 deg C, 5 h 2: 95 percent / CH2Cl2 / 15 h / -45 °C 3: 63 percent / Burgess' reagent 4: 100 percent / pyridine 5: 65 percent / OsO4 6: DBU / toluene / 2 h / 105 °C 7: 75 percent / pyridine, DMAP / 24 h / 25 °C 8: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 9: tetrahydrofuran / 0.17 h / -78 °C 10: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 11: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 12: pyridine, DMAP / 20 h / 25 °C 13: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 14: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 15: HF, pyridine / acetonitrile / 1 h / 0 °C 16: H2 / Pd/C / ethanol / 1 h View Scheme

1: 100 percent / pyridine 2: 65 percent / OsO4 3: DBU / toluene / 2 h / 105 °C 4: 75 percent / pyridine, DMAP / 24 h / 25 °C 5: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 6: tetrahydrofuran / 0.17 h / -78 °C 7: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 8: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 9: pyridine, DMAP / 20 h / 25 °C 10: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 11: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 12: HF, pyridine / acetonitrile / 1 h / 0 °C 13: H2 / Pd/C / ethanol / 1 h View Scheme