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

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