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: 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 View Scheme