(+)-(3As,6as)-3a,6a-二氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮合成路线 （共 95 条）
反应条件
1: 98 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C
2: 96 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C
3: 76 percent / acetic acid / 96 h / 60 °C
View Scheme
参考文献
Nakashima, Hiromi; Sato, Masayuki; Taniguchi, Takahiko; Ogasawara, Kunio
Synthesis, 2000 , # 6 p. 817 - 823
反应条件
1: 1.) K2Os(OH)4, (DHQD)2PHAL, K3Fe(CN)6, K2CO3, CH3SO2NH2, 2.) Na2SO3 / 1.) H2O, t-BuOH, 22 h, 2.) H2O, t-BuOH, 15 min
2: 85 percent / p-TsOH / acetone / 1 h
3: 1.) K2Os(OH)4, quinuclidine, K3Fe(CN)6, K2CO3, CH3SO2NH2, 2.) Na2SO3 / 1.) H2O, t-BuOH, 46 h, 2.) H2O, t-BuOH, 60 min
4: NaIO4 / tetrahydrofuran; H2O / 18 h / 55 °C
View Scheme
参考文献
Armstrong, Alan; Hayter, Barry R.
Tetrahedron Asymmetry, 1997 , vol. 8, # 10 p. 1677 - 1684
反应条件
1: 1.) K2Os(OH)4, (DHQD)2PHAL, K3Fe(CN)6, K2CO3, CH3SO2NH2, 2.) Na2SO3 / 1.) H2O, t-BuOH, 22 h, 2.) H2O, t-BuOH, 15 min
2: 93 percent / p-TsOH / CH2Cl2 / 3 h / Ambient temperature
3: 1.) K2Os(OH)4, quinuclidine, K3Fe(CN)6, K2CO3, CH3SO2NH2, 2.) Na2SO3, 3.) NaIO4
View Scheme
参考文献
Armstrong, Alan; Hayter, Barry R.
Tetrahedron Asymmetry, 1997 , vol. 8, # 10 p. 1677 - 1684
反应条件
1: 93 percent / p-TsOH / CH2Cl2 / 3 h / Ambient temperature
2: 1.) K2Os(OH)4, quinuclidine, K3Fe(CN)6, K2CO3, CH3SO2NH2, 2.) Na2SO3, 3.) NaIO4
View Scheme
参考文献
Armstrong, Alan; Hayter, Barry R.
Tetrahedron Asymmetry, 1997 , vol. 8, # 10 p. 1677 - 1684
反应条件
1: 1.) K2Os(OH)4, quinuclidine, K3Fe(CN)6, K2CO3, CH3SO2NH2, 2.) Na2SO3 / 1.) H2O, t-BuOH, 46 h, 2.) H2O, t-BuOH, 60 min
2: NaIO4 / tetrahydrofuran; H2O / 18 h / 55 °C
View Scheme
参考文献
Armstrong, Alan; Hayter, Barry R.
Tetrahedron Asymmetry, 1997 , vol. 8, # 10 p. 1677 - 1684
反应条件
1: 38 percent / hexane / 24 h / 40 - 45 °C / Pseudomonas cepacia lipase (PS-30 Lipase)
2: aq. OsO4, N-methylmorpholine-N-oxide / tetrahydrofuran; acetone / 24 h
3: TsOH / acetone / 18 h
4: 100 percent / methanol. KOH / 0.5 h / Ambient temperature
5: pyridinium chlorochromate, pyridine, molecular sieves / CH2Cl2
View Scheme
参考文献
Biadatti, Thibaud; Esker, John L.; Johnson, Carl R.
Tetrahedron Asymmetry, 1996 , vol. 7, # 8 p. 2313 - 2320
反应条件
1: aq. OsO4, N-methylmorpholine-N-oxide / tetrahydrofuran; acetone / 24 h
2: TsOH / acetone / 18 h
3: 100 percent / methanol. KOH / 0.5 h / Ambient temperature
4: pyridinium chlorochromate, pyridine, molecular sieves / CH2Cl2
View Scheme
参考文献
Biadatti, Thibaud; Esker, John L.; Johnson, Carl R.
Tetrahedron Asymmetry, 1996 , vol. 7, # 8 p. 2313 - 2320
反应条件
1: 100 percent / methanol. KOH / 0.5 h / Ambient temperature
2: pyridinium chlorochromate, pyridine, molecular sieves / CH2Cl2
View Scheme
参考文献
Biadatti, Thibaud; Esker, John L.; Johnson, Carl R.
Tetrahedron Asymmetry, 1996 , vol. 7, # 8 p. 2313 - 2320
反应条件
1: Et3N / tetrahydrofuran
2: aq. OsO4, N-methylmorpholine-N-oxide / tetrahydrofuran; acetone / 24 h
3: TsOH / acetone / 18 h
4: 86 percent / aq. ceric ammonium nitrate / acetonitrile / 0.08 h / 0 °C
5: 78 percent / pyridinium chlorochromate, pyridine, molecular sieves / CH2Cl2
View Scheme
参考文献
Biadatti, Thibaud; Esker, John L.; Johnson, Carl R.
Tetrahedron Asymmetry, 1996 , vol. 7, # 8 p. 2313 - 2320
反应条件
1: aq. OsO4, N-methylmorpholine-N-oxide / tetrahydrofuran; acetone / 24 h
2: TsOH / acetone / 18 h
3: 100 percent / methanol. KOH / 0.5 h / Ambient temperature
4: 72 percent / pyridinium chlorochromate, pyridine, molecular sieves / CH2Cl2
View Scheme
参考文献
Biadatti, Thibaud; Esker, John L.; Johnson, Carl R.
Tetrahedron Asymmetry, 1996 , vol. 7, # 8 p. 2313 - 2320
