pyridinium p-toluenesulfonate in acetone 2 h; Heating;

1: 1.) Mg / 1.) ether, 2.) ether, 8 h, RT 2: 54 percent / I2 / CHCl3 / 2 h / Heating 3: 1.) O3, 2.) LiAlH4 / 1.) hexane, -45 deg C, 2.) hexane, ether, from -45 to -35 deg C 4: 94 percent / Br2, NaHCO3, HMPA / CH2Cl2 / 0 °C 5: 95 percent / TosOH*H2O / toluene / 2 h / Heating 6: 90 percent / pyridine / 40 h / 4 °C 7: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 8: 98 percent / 2 h / Heating 9: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 10: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 11: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 12: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 13: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 94 percent / Br2, NaHCO3, HMPA / CH2Cl2 / 0 °C 2: 95 percent / TosOH*H2O / toluene / 2 h / Heating 3: 90 percent / pyridine / 40 h / 4 °C 4: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 5: 98 percent / 2 h / Heating 6: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 7: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 8: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 9: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 10: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 1.) O3, 2.) LiAlH4 / 1.) hexane, -45 deg C, 2.) hexane, ether, from -45 to -35 deg C 2: 94 percent / Br2, NaHCO3, HMPA / CH2Cl2 / 0 °C 3: 95 percent / TosOH*H2O / toluene / 2 h / Heating 4: 90 percent / pyridine / 40 h / 4 °C 5: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 6: 98 percent / 2 h / Heating 7: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 8: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 9: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 10: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 11: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 54 percent / I2 / CHCl3 / 2 h / Heating 2: 1.) O3, 2.) LiAlH4 / 1.) hexane, -45 deg C, 2.) hexane, ether, from -45 to -35 deg C 3: 94 percent / Br2, NaHCO3, HMPA / CH2Cl2 / 0 °C 4: 95 percent / TosOH*H2O / toluene / 2 h / Heating 5: 90 percent / pyridine / 40 h / 4 °C 6: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 7: 98 percent / 2 h / Heating 8: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 9: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 10: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 11: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 12: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 95 percent / TosOH*H2O / toluene / 2 h / Heating 2: 90 percent / pyridine / 40 h / 4 °C 3: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 4: 98 percent / 2 h / Heating 5: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 6: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 7: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 8: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 9: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 90 percent / pyridine / 40 h / 4 °C 2: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h 3: 98 percent / 2 h / Heating 4: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 5: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 6: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 7: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 8: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 1.) TosOH*H2O, ethylene glycol, 2.) H2, 5percent Pd on charcoal / 1.) CH2Cl2, toluene, 1 h, reflux, 2.) AcOEt, 30 h, RT 2: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C 3: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT 4: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 5: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 6: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme

1: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C 2: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux 3: 86 percent / pyridinium p-toluenesulfonate / acetone / 2 h / Heating View Scheme