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: 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 View Scheme