(+)-(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: (Ph3P)4Pd / tetrahydrofuran / 12 h
2: 38 percent / hexane / 24 h / 40 - 45 °C / Pseudomonas cepacia lipase (PS-30 Lipase)
3: aq. OsO4, N-methylmorpholine-N-oxide / tetrahydrofuran; acetone / 24 h
4: TsOH / acetone / 18 h
5: 100 percent / methanol. KOH / 0.5 h / Ambient temperature
6: 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: 94 percent / N-methylmorpholine N-oxide (NMO), OsO4 / acetone; H2O
2: 79 percent / p-toluenesulfonic acid (p-TSA) / acetone / Ambient temperature
3: 80 percent / pyridinium chlorochromate, diatomaceous earth / CH2Cl2 / 48 h / Ambient temperature
View Scheme
参考文献
Deardorff, Donald R.; Shambayati, Soroosh; Myles, David C.; Heerding, Dirk
Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3614 - 3615
反应条件
1: 79 percent / p-toluenesulfonic acid (p-TSA) / acetone / Ambient temperature
2: 80 percent / pyridinium chlorochromate, diatomaceous earth / CH2Cl2 / 48 h / Ambient temperature
View Scheme
参考文献
Deardorff, Donald R.; Shambayati, Soroosh; Myles, David C.; Heerding, Dirk
Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3614 - 3615
反应条件
1: 56 percent / pyridinium chlorochromate / benzene / Heating
2: 80 percent
View Scheme
参考文献
Ali, Syed Mashhood; Ramesh, Kakarla; Borchardt, Ronald T.
Tetrahedron Letters, 1990 , vol. 31, # 11 p. 1509 - 1512
反应条件
pyridine; methanesulfonyl chloride in dichloromethane
Yield given;
参考文献
Belanger, Pascale; Prasit, Petpiboon
Tetrahedron Letters, 1988 , vol. 29, # 43 p. 5521 - 5524
反应条件
1: 92 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
2: 95 percent / aq. NaIO4 / 0.5 h / 20 °C
View Scheme
参考文献
Chu; Jin; Baker; Huggins
Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 1 p. 9 - 12
反应条件
1: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
2: 95 percent / aq. NaIO4 / 0.5 h / 20 °C
View Scheme
参考文献
Chu; Jin; Baker; Huggins
Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 1 p. 9 - 12
反应条件
1: 13.51 g / aq. NaIO4 / CH2Cl2 / 0.5 h / 20 °C
2: 88 percent / Grubbs catalyst / CHCl3 / 6 h / 20 °C
3: 85 percent / MnO2 / CH2Cl2 / 20 °C
View Scheme
参考文献
Moon, Hyung Ryong; Choi, Won Jun; Kim, Hea Ok; Jeong, Lak Shin
Tetrahedron Asymmetry, 2002 , vol. 13, # 11 p. 1189 - 1193
反应条件
1: 96 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C
2: 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: 97 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C
2: 78 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
