1: 78 percent / 1.) PhSeCl, 2.) Ra-Ni(W-2) / 1.) CH2Cl2, 0 deg C, 38 h, 2.) EtOH, reflux, 5 min 2: 97 percent / n-Bu4NF / tetrahydrofuran / 5 h / 23 °C 3: 89 percent / n-Bu3P / tetrahydrofuran / 0.5 h / 23 °C 4: 84 percent / 30percent H2O2 / CH2Cl2 / 20 h / 18 °C 5: 96 percent / 1.) DDQ, 2.) K2CO3 / 1.) CH2Cl2 - H2O, 23 deg C, 48 h, 2.) MeOH, 23 deg C, 40 min 6: 77 percent / aq. HClO4; tetrahydrofuran / 60 h / 23 °C 7: 85 percent / pyridine / 9 h / 0 °C View Scheme

Multi-step reaction with 26 steps 1: tetrahydrofuran / 0.5 h / -78 °C2: H2, quinoline / Lindlar catalyst / benzene / 2 h / 25 °C3: DMAP / CH2Cl2 / 2 h / Heating4: 35 percent / Pd(PPh3)4, Et3N / tetrahydrofuran / 5 h / Heating5: 25 percent / toluene / 5 h / 220 - 230 °C / in sealed tube6: 90 percent / OsO4, Me3NO, pyridine / 2-methyl-propan-2-ol; H2O / 18 h / Heating7: 81 percent / SO3-pyridine, Et3N / 20 h / 20 °C8: 85 percent / NaTeH / ethanol / 0.5 h / 23 °C9: 87 percent / t-BuNH3-BH3 / methanol / 21 h / 23 °C10: 95 percent / TsOH / benzene / 1 h / 23 °C11: 94 percent / MCPBA / CH2Cl2 / 0.5 h / -25 °C12: 68 percent / CaCO3 / toluene / 70 h / Heating13: 92 percent / LiOMe / tetrahydrofuran / 72 h / 23 °C14: 89 percent / LiAlH4 / diethyl ether / 1 h / Heating15: 90 percent / DMAP / 1,2-dichloro-ethane / 6 h / Heating16: 83 percent / 1.) OsO4, 2.) H2S / 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h17: 91 percent / NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / 23 °C18: 95 percent / TsOH / CHCl3; methanol / 0.67 h / 20 °C19: 96 percent / pyridine / 2 h / 20 °C20: 95 percent / TsOH / 0.25 h / 20 °C21: 95 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C22: 78 percent / SO3-pyridine, Et3N / dimethylsulfoxide / 16 h / 23 °C23: 80 percent / tetrahydrofuran / 2 h / -78 - 20 °C24: 79 percent / MnO2 / benzene / 3 h / 23 °C25: 93 percent / diethyl ether / 0.25 h / -78 °C26: 95 percent / 1.) 3 N HCl - THF, 23 deg C, 1 h, then 0.2 N KOH - THF - MeOH, 23 deg C, 20 min  

Multi-step reaction with 14 steps 1: 92 percent / LiOMe / tetrahydrofuran / 72 h / 23 °C2: 89 percent / LiAlH4 / diethyl ether / 1 h / Heating3: 90 percent / DMAP / 1,2-dichloro-ethane / 6 h / Heating4: 83 percent / 1.) OsO4, 2.) H2S / 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h5: 91 percent / NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / 23 °C6: 95 percent / TsOH / CHCl3; methanol / 0.67 h / 20 °C7: 96 percent / pyridine / 2 h / 20 °C8: 95 percent / TsOH / 0.25 h / 20 °C9: 95 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C10: 78 percent / SO3-pyridine, Et3N / dimethylsulfoxide / 16 h / 23 °C11: 80 percent / tetrahydrofuran / 2 h / -78 - 20 °C12: 79 percent / MnO2 / benzene / 3 h / 23 °C13: 93 percent / diethyl ether / 0.25 h / -78 °C14: 95 percent / 1.) 3 N HCl - THF, 23 deg C, 1 h, then 0.2 N KOH - THF - MeOH, 23 deg C, 20 min  

Multi-step reaction with 13 steps 1: 89 percent / LiAlH4 / diethyl ether / 1 h / Heating2: 90 percent / DMAP / 1,2-dichloro-ethane / 6 h / Heating3: 83 percent / 1.) OsO4, 2.) H2S / 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h4: 91 percent / NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / 23 °C5: 95 percent / TsOH / CHCl3; methanol / 0.67 h / 20 °C6: 96 percent / pyridine / 2 h / 20 °C7: 95 percent / TsOH / 0.25 h / 20 °C8: 95 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C9: 78 percent / SO3-pyridine, Et3N / dimethylsulfoxide / 16 h / 23 °C10: 80 percent / tetrahydrofuran / 2 h / -78 - 20 °C11: 79 percent / MnO2 / benzene / 3 h / 23 °C12: 93 percent / diethyl ether / 0.25 h / -78 °C13: 95 percent / 1.) 3 N HCl - THF, 23 deg C, 1 h, then 0.2 N KOH - THF - MeOH, 23 deg C, 20 min  

Multi-step reaction with 21 steps 1: 90 percent / OsO4, Me3NO, pyridine / 2-methyl-propan-2-ol; H2O / 18 h / Heating2: 81 percent / SO3-pyridine, Et3N / 20 h / 20 °C3: 85 percent / NaTeH / ethanol / 0.5 h / 23 °C4: 87 percent / t-BuNH3-BH3 / methanol / 21 h / 23 °C5: 95 percent / TsOH / benzene / 1 h / 23 °C6: 94 percent / MCPBA / CH2Cl2 / 0.5 h / -25 °C7: 68 percent / CaCO3 / toluene / 70 h / Heating8: 92 percent / LiOMe / tetrahydrofuran / 72 h / 23 °C9: 89 percent / LiAlH4 / diethyl ether / 1 h / Heating10: 90 percent / DMAP / 1,2-dichloro-ethane / 6 h / Heating11: 83 percent / 1.) OsO4, 2.) H2S / 1.) pyridine, 20 deg C, 30 h, 2.) chloroform - dioxane, 23 deg C, 0.5 h12: 91 percent / NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / 23 °C13: 95 percent / TsOH / CHCl3; methanol / 0.67 h / 20 °C14: 96 percent / pyridine / 2 h / 20 °C15: 95 percent / TsOH / 0.25 h / 20 °C16: 95 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C17: 78 percent / SO3-pyridine, Et3N / dimethylsulfoxide / 16 h / 23 °C18: 80 percent / tetrahydrofuran / 2 h / -78 - 20 °C19: 79 percent / MnO2 / benzene / 3 h / 23 °C20: 93 percent / diethyl ether / 0.25 h / -78 °C21: 95 percent / 1.) 3 N HCl - THF, 23 deg C, 1 h, then 0.2 N KOH - THF - MeOH, 23 deg C, 20 min