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: 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 View Scheme