1: DIBAL / CH2Cl2 / -78 °C 2: 2,6-lutidine / CH2Cl2 / -23 °C 3: O2, TPP / CH2Cl2 / Irradiation 4: Bu3SnH, AIBN / benzene / Heating 5: H2 / Pd/C / ethanol 6: CSA / CH2Cl2 / -23 °C 7: 66 percent / Et2Zn / toluene / 0 °C 8: 77 percent / Dess-Martin reagent / CH2Cl2 9: 84 percent / H2 / Pd(OH)2 / ethanol 10: pyridine / CH2Cl2 / -45 °C 11: TBAF, AcOH / tetrahydrofuran 12: 86 percent / PPTS / benzene / Heating 13: 100 percent / K2CO3 / methanol; tetrahydrofuran 14: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 15: TBAF, BHT / tetrahydrofuran 16: NaOMe, BHT / methanol 17: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 18: 92 percent / Dess-Martin reagent / CH2Cl2 19: 89 percent / PPTS / CH2Cl2 20: 89 percent / KHMDS / -78 °C 21: 91 percent / Pd(PPh3)4 / diethyl ether 22: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 23: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 24: 92 percent / DMAP / CH2Cl2 25: 68 percent / DBN / toluene / Heating 26: 86 percent / OsO4, pyridine / diethyl ether 27: 86 percent / DBU / toluene / Heating 28: PPTS, MeOH 29: imidazole / dimethylformamide 30: 97 percent / H2 / Pd(OH)2 / ethanol 31: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 32: 66 percent / DMAP / CH2Cl2 33: 83 percent / tetrahydrofuran / -78 °C 34: 88 percent / HF*pyridine / tetrahydrofuran 35: 94 percent / pyridine / CH2Cl2 36: 80 percent / TASF / tetrahydrofuran 37: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 38: 84 percent / Zn, aq. AcOH View Scheme

1: 2,6-lutidine / CH2Cl2 / -23 °C 2: O2, TPP / CH2Cl2 / Irradiation 3: Bu3SnH, AIBN / benzene / Heating 4: H2 / Pd/C / ethanol 5: CSA / CH2Cl2 / -23 °C 6: 66 percent / Et2Zn / toluene / 0 °C 7: 77 percent / Dess-Martin reagent / CH2Cl2 8: 84 percent / H2 / Pd(OH)2 / ethanol 9: pyridine / CH2Cl2 / -45 °C 10: TBAF, AcOH / tetrahydrofuran 11: 86 percent / PPTS / benzene / Heating 12: 100 percent / K2CO3 / methanol; tetrahydrofuran 13: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 14: TBAF, BHT / tetrahydrofuran 15: NaOMe, BHT / methanol 16: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 17: 92 percent / Dess-Martin reagent / CH2Cl2 18: 89 percent / PPTS / CH2Cl2 19: 89 percent / KHMDS / -78 °C 20: 91 percent / Pd(PPh3)4 / diethyl ether 21: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 22: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 23: 92 percent / DMAP / CH2Cl2 24: 68 percent / DBN / toluene / Heating 25: 86 percent / OsO4, pyridine / diethyl ether 26: 86 percent / DBU / toluene / Heating 27: PPTS, MeOH 28: imidazole / dimethylformamide 29: 97 percent / H2 / Pd(OH)2 / ethanol 30: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 31: 66 percent / DMAP / CH2Cl2 32: 83 percent / tetrahydrofuran / -78 °C 33: 88 percent / HF*pyridine / tetrahydrofuran 34: 94 percent / pyridine / CH2Cl2 35: 80 percent / TASF / tetrahydrofuran 36: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 37: 84 percent / Zn, aq. AcOH View Scheme

1: CSA / CH2Cl2 / -23 °C 2: 66 percent / Et2Zn / toluene / 0 °C 3: 77 percent / Dess-Martin reagent / CH2Cl2 4: 84 percent / H2 / Pd(OH)2 / ethanol 5: pyridine / CH2Cl2 / -45 °C 6: TBAF, AcOH / tetrahydrofuran 7: 86 percent / PPTS / benzene / Heating 8: 100 percent / K2CO3 / methanol; tetrahydrofuran 9: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 10: TBAF, BHT / tetrahydrofuran 11: NaOMe, BHT / methanol 12: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 13: 92 percent / Dess-Martin reagent / CH2Cl2 14: 89 percent / PPTS / CH2Cl2 15: 89 percent / KHMDS / -78 °C 16: 91 percent / Pd(PPh3)4 / diethyl ether 17: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 18: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 19: 92 percent / DMAP / CH2Cl2 20: 68 percent / DBN / toluene / Heating 21: 86 percent / OsO4, pyridine / diethyl ether 22: 86 percent / DBU / toluene / Heating 23: PPTS, MeOH 24: imidazole / dimethylformamide 25: 97 percent / H2 / Pd(OH)2 / ethanol 26: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 27: 66 percent / DMAP / CH2Cl2 28: 83 percent / tetrahydrofuran / -78 °C 29: 88 percent / HF*pyridine / tetrahydrofuran 30: 94 percent / pyridine / CH2Cl2 31: 80 percent / TASF / tetrahydrofuran 32: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 33: 84 percent / Zn, aq. AcOH View Scheme

1: 1.) (MeBO)3, pyridine, 2.) TiCl2(OiPr)2, 3.) pinacol, DMAP 2: BuLi / tetrahydrofuran / -78 - 0 °C 3: DIBAL / CH2Cl2 / -78 °C 4: 2,6-lutidine / CH2Cl2 / -23 °C 5: O2, TPP / CH2Cl2 / Irradiation 6: Bu3SnH, AIBN / benzene / Heating 7: H2 / Pd/C / ethanol 8: CSA / CH2Cl2 / -23 °C 9: 66 percent / Et2Zn / toluene / 0 °C 10: 77 percent / Dess-Martin reagent / CH2Cl2 11: 84 percent / H2 / Pd(OH)2 / ethanol 12: pyridine / CH2Cl2 / -45 °C 13: TBAF, AcOH / tetrahydrofuran 14: 86 percent / PPTS / benzene / Heating 15: 100 percent / K2CO3 / methanol; tetrahydrofuran 16: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 17: TBAF, BHT / tetrahydrofuran 18: NaOMe, BHT / methanol 19: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 20: 92 percent / Dess-Martin reagent / CH2Cl2 21: 89 percent / PPTS / CH2Cl2 22: 89 percent / KHMDS / -78 °C 23: 91 percent / Pd(PPh3)4 / diethyl ether 24: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 25: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 26: 92 percent / DMAP / CH2Cl2 27: 68 percent / DBN / toluene / Heating 28: 86 percent / OsO4, pyridine / diethyl ether 29: 86 percent / DBU / toluene / Heating 30: PPTS, MeOH 31: imidazole / dimethylformamide 32: 97 percent / H2 / Pd(OH)2 / ethanol 33: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 34: 66 percent / DMAP / CH2Cl2 35: 83 percent / tetrahydrofuran / -78 °C 36: 88 percent / HF*pyridine / tetrahydrofuran 37: 94 percent / pyridine / CH2Cl2 38: 80 percent / TASF / tetrahydrofuran 39: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 40: 84 percent / Zn, aq. AcOH View Scheme

1: O2, TPP / CH2Cl2 / Irradiation 2: Bu3SnH, AIBN / benzene / Heating 3: H2 / Pd/C / ethanol 4: CSA / CH2Cl2 / -23 °C 5: 66 percent / Et2Zn / toluene / 0 °C 6: 77 percent / Dess-Martin reagent / CH2Cl2 7: 84 percent / H2 / Pd(OH)2 / ethanol 8: pyridine / CH2Cl2 / -45 °C 9: TBAF, AcOH / tetrahydrofuran 10: 86 percent / PPTS / benzene / Heating 11: 100 percent / K2CO3 / methanol; tetrahydrofuran 12: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 13: TBAF, BHT / tetrahydrofuran 14: NaOMe, BHT / methanol 15: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 16: 92 percent / Dess-Martin reagent / CH2Cl2 17: 89 percent / PPTS / CH2Cl2 18: 89 percent / KHMDS / -78 °C 19: 91 percent / Pd(PPh3)4 / diethyl ether 20: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 21: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 22: 92 percent / DMAP / CH2Cl2 23: 68 percent / DBN / toluene / Heating 24: 86 percent / OsO4, pyridine / diethyl ether 25: 86 percent / DBU / toluene / Heating 26: PPTS, MeOH 27: imidazole / dimethylformamide 28: 97 percent / H2 / Pd(OH)2 / ethanol 29: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 30: 66 percent / DMAP / CH2Cl2 31: 83 percent / tetrahydrofuran / -78 °C 32: 88 percent / HF*pyridine / tetrahydrofuran 33: 94 percent / pyridine / CH2Cl2 34: 80 percent / TASF / tetrahydrofuran 35: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 36: 84 percent / Zn, aq. AcOH View Scheme

1: H2 / Pd/C / ethanol 2: CSA / CH2Cl2 / -23 °C 3: 66 percent / Et2Zn / toluene / 0 °C 4: 77 percent / Dess-Martin reagent / CH2Cl2 5: 84 percent / H2 / Pd(OH)2 / ethanol 6: pyridine / CH2Cl2 / -45 °C 7: TBAF, AcOH / tetrahydrofuran 8: 86 percent / PPTS / benzene / Heating 9: 100 percent / K2CO3 / methanol; tetrahydrofuran 10: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 11: TBAF, BHT / tetrahydrofuran 12: NaOMe, BHT / methanol 13: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 14: 92 percent / Dess-Martin reagent / CH2Cl2 15: 89 percent / PPTS / CH2Cl2 16: 89 percent / KHMDS / -78 °C 17: 91 percent / Pd(PPh3)4 / diethyl ether 18: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 19: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 20: 92 percent / DMAP / CH2Cl2 21: 68 percent / DBN / toluene / Heating 22: 86 percent / OsO4, pyridine / diethyl ether 23: 86 percent / DBU / toluene / Heating 24: PPTS, MeOH 25: imidazole / dimethylformamide 26: 97 percent / H2 / Pd(OH)2 / ethanol 27: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 28: 66 percent / DMAP / CH2Cl2 29: 83 percent / tetrahydrofuran / -78 °C 30: 88 percent / HF*pyridine / tetrahydrofuran 31: 94 percent / pyridine / CH2Cl2 32: 80 percent / TASF / tetrahydrofuran 33: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 34: 84 percent / Zn, aq. AcOH View Scheme

1: Bu3SnH, AIBN / benzene / Heating 2: H2 / Pd/C / ethanol 3: CSA / CH2Cl2 / -23 °C 4: 66 percent / Et2Zn / toluene / 0 °C 5: 77 percent / Dess-Martin reagent / CH2Cl2 6: 84 percent / H2 / Pd(OH)2 / ethanol 7: pyridine / CH2Cl2 / -45 °C 8: TBAF, AcOH / tetrahydrofuran 9: 86 percent / PPTS / benzene / Heating 10: 100 percent / K2CO3 / methanol; tetrahydrofuran 11: 100 percent / SmI2, HMPA / tetrahydrofuran; methanol 12: TBAF, BHT / tetrahydrofuran 13: NaOMe, BHT / methanol 14: 1.) PhB(OH)2, 2.) 2,6-lutidine, 3.) H2O2, NaHCO3 15: 92 percent / Dess-Martin reagent / CH2Cl2 16: 89 percent / PPTS / CH2Cl2 17: 89 percent / KHMDS / -78 °C 18: 91 percent / Pd(PPh3)4 / diethyl ether 19: 1.) NCS, 2.) 2-methoxypropene, PPTS / 1.) MeOH, 2.) CH2Cl2 20: 1.) LDA, 2.) MoO5*pyr*HMPA / 1.) THF, -23 deg C, 2.) THF, -23 deg C 21: 92 percent / DMAP / CH2Cl2 22: 68 percent / DBN / toluene / Heating 23: 86 percent / OsO4, pyridine / diethyl ether 24: 86 percent / DBU / toluene / Heating 25: PPTS, MeOH 26: imidazole / dimethylformamide 27: 97 percent / H2 / Pd(OH)2 / ethanol 28: 94 percent / pyridine / CH2Cl2 / -78 - 0 °C 29: 66 percent / DMAP / CH2Cl2 30: 83 percent / tetrahydrofuran / -78 °C 31: 88 percent / HF*pyridine / tetrahydrofuran 32: 94 percent / pyridine / CH2Cl2 33: 80 percent / TASF / tetrahydrofuran 34: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 35: 84 percent / Zn, aq. AcOH View Scheme

1: tetrahydrofuran / 0.17 h / -78 °C 2: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 3: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 4: pyridine, DMAP / 20 h / 25 °C 5: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 6: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 7: HF, pyridine / acetonitrile / 1 h / 0 °C 8: H2 / Pd/C / ethanol / 1 h View Scheme

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

1: Et3N / -78 °C 2: LDA / 3 h / -35 °C 3: HOAc / 14 h / 0 °C 4: DBU / toluene / 2 h / 105 °C 5: 75 percent / pyridine, DMAP / 24 h / 25 °C 6: 100 percent / HF*pyridine / acetonitrile / 11 h / 0 °C 7: tetrahydrofuran / 0.17 h / -78 °C 8: tetrapropylammonium perruthenate, NMO, molecular sieves / CH2Cl2 / 0.25 h / 25 °C 9: 1.) t-BuOK, 2.) benzeneseleninic anhydride, 3.) t-BuOK 10: pyridine, DMAP / 20 h / 25 °C 11: 94 percent / TASF / tetrahydrofuran / 1 h / 25 °C 12: 1.) LHMDS / 1.) THF, 2.) THF, 0 deg C, 1 h 13: HF, pyridine / acetonitrile / 1 h / 0 °C 14: H2 / Pd/C / ethanol / 1 h View Scheme