(4R,5R)-rel-4,5-二羟基-5-(羟基甲基)-2-环戊烯-1-酮合成路线 （共 19 条）
反应条件
1: 53 percent / SeO2 / 2-methyl-propan-2-ol; benzene / Heating
2: 96 percent / acetic acid (glacial) / tetrahydrofuran; H2O / 80 h / Ambient temperature
View Scheme
参考文献
Smith III; Branca; Pilla; Guaciaro
Journal of Organic Chemistry, 1982 , vol. 47, # 10 p. 1855 - 1869
反应条件
1: 40 percent / imidazole / dimethylformamide / 5 h
2: 1.) osmium(VIII) oxide, 2.) sodium bisulphite, water / 1.) pyridine, 45 min, 2.) 4 h
3: 54 percent / 3 M hydrochloric acid / tetrahydrofuran / 4 h
View Scheme
参考文献
Hetmanski, Michael; Purcell, Neil; Stoodley, Richard J.; Palfreyman, Malcolm N.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , p. 2089 - 2096
反应条件
1: 1.) osmium(VIII) oxide, 2.) sodium bisulphite, water / 1.) pyridine, 45 min, 2.) 4 h
2: 54 percent / 3 M hydrochloric acid / tetrahydrofuran / 4 h
View Scheme
参考文献
Hetmanski, Michael; Purcell, Neil; Stoodley, Richard J.; Palfreyman, Malcolm N.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , p. 2089 - 2096
反应条件
1: 51 percent / SeO2 / 2-methyl-propan-2-ol; benzene / 140 h / Heating
2: 94 percent / acetic acid (glacial) / tetrahydrofuran; H2O / 82 h / Ambient temperature
View Scheme
参考文献
Smith III; Branca; Pilla; Guaciaro
Journal of Organic Chemistry, 1982 , vol. 47, # 10 p. 1855 - 1869
反应条件
1: 100 percent / NaIO4 / methanol; H2O / 10 h / 0 deg C to r.t.
2: LDA / tetrahydrofuran / 1) -78 deg C, 2 h 2) 0 deg C, 2 h
3: 33 percent / 340 °C / 0.1 Torr / flash vacuum pyrolysis
4: 100 percent / 90percent CF3CO2H
View Scheme
参考文献
Pohmakotr; Popuang
Tetrahedron Letters, 1991 , vol. 32, # 2 p. 275 - 278
反应条件
1: LDA / tetrahydrofuran / 1) -78 deg C, 2 h 2) 0 deg C, 2 h
2: 33 percent / 340 °C / 0.1 Torr / flash vacuum pyrolysis
3: 100 percent / 90percent CF3CO2H
View Scheme
参考文献
Pohmakotr; Popuang
Tetrahedron Letters, 1991 , vol. 32, # 2 p. 275 - 278
反应条件
methanol; hydrogen cation
2.) 525 deg C, 0.04 Torr; Yield given. Multistep reaction;
参考文献
Verlaak; Klunder; Zwanenburg
Tetrahedron Letters, 1982 , vol. 23, # 51 p. 5463 - 5466
反应条件
1: 1.) DMAP 2.) AgOAc / 1.) -15 deg C 2.) HOAc
2: 1.) CH3OH/H(1+) / 2.) 525 deg C, 0.04 Torr
View Scheme
参考文献
Verlaak; Klunder; Zwanenburg
Tetrahedron Letters, 1982 , vol. 23, # 51 p. 5463 - 5466
反应条件
1: 33 percent / 340 °C / 0.1 Torr / flash vacuum pyrolysis
2: 100 percent / 90percent CF3CO2H
View Scheme
参考文献
Pohmakotr; Popuang
Tetrahedron Letters, 1991 , vol. 32, # 2 p. 275 - 278
