Clasto-lactacystin (Omuralide)合成路线 （共 96 条）
反应条件
1: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C 2: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 3: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 4: NaBH4 / methanol / 20 °C 5: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 6: 100 percent / tetrahydrofuran / Heating 7: n-Bu3SnH; AIBN / toluene / Heating 8: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 9: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 10: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 11: 74 percent / NaOMe / methanol / 20 °C 12: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 2: 100 percent / tetrahydrofuran / Heating 3: n-Bu3SnH; AIBN / toluene / Heating 4: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 5: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 6: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 7: 74 percent / NaOMe / methanol / 20 °C 8: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: NaBH4 / methanol / 20 °C 2: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 3: 100 percent / tetrahydrofuran / Heating 4: n-Bu3SnH; AIBN / toluene / Heating 5: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 6: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 7: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 8: 74 percent / NaOMe / methanol / 20 °C 9: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 2: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 3: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 4: 74 percent / NaOMe / methanol / 20 °C 5: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 2: 74 percent / NaOMe / methanol / 20 °C 3: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 2: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 3: 74 percent / NaOMe / methanol / 20 °C 4: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 100 percent / tetrahydrofuran / Heating 2: n-Bu3SnH; AIBN / toluene / Heating 3: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 4: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 5: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 6: 74 percent / NaOMe / methanol / 20 °C 7: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 74 percent / NaOMe / methanol / 20 °C 2: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: n-Bu3SnH; AIBN / toluene / Heating 2: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 3: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 4: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 5: 74 percent / NaOMe / methanol / 20 °C 6: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1.1: ruthenium(IV) oxide hydrate; sodium periodate / CCl4; acetonitrile; H2O / 3 h / 20 °C 2.1: 2.13 g / methanol; toluene / 1 h / 0 °C 3.1: 86 percent / K2CO3 / CH2Cl2 / 3 h / 0 °C 4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C 4.2: 71 percent / tetrahydrofuran / 0.17 h 5.1: 95 percent / borontrifluoride etherate / CH2Cl2 / 4 h / 20 °C 6.1: p-TsOH / CH2Cl2 / 3 h / 20 °C 7.1: DMAP / CH2Cl2 / 12 h / 20 °C 8.1: 85 percent / p-TsOH / methanol / 12 h / 20 °C 9.1: 88 percent / LDA; HMPA / tetrahydrofuran / 4 h / -78 °C 10.1: 75 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C 11.1: aq. NaOH / 72 h / 20 °C 12.1: 16 mg / triethylamine; bis(2-oxo-3-oxazolidinyl)phosphonic chloride / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
European Journal of Organic Chemistry, , # 1 p. 37 - 39
