(+)-(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: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h
2: 1.) n-BuLi, triphenylmethane / 1.) hexane-THF, 0 deg C, 15 min; 2.) hexane-THF, -78 deg C,15 min
3: 98 percent / silica gel / toluene / 9 h / Heating
View Scheme
参考文献
Johnson; Penning
Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4726 - 4735
反应条件
1: 84 percent / triphenylphosphite/O3 / CH2Cl2 / 1.) -78 deg C; 2.) 0 deg C, 20 min
2: 96 percent / aluminum/mercuric chloride / diethyl ether; methanol; H2O / 0.42 h
3: 81 percent / phosphate buffer (pH 8), osmium tetraoxide, sodium periodate / dioxane / 1.) 0 deg C, 1 h; 2.) room temperature, 20 h
4: neutral alumina / 1,2-dimethoxy-ethane / 0.25 h / Heating
5: 64.6 percent / neutral alumina / 1,2-dimethoxy-ethane / 0.75 h / Heating
View Scheme
参考文献
Hudlicky; Luna; Barbieri; Kwart
Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4735 - 4741
反应条件
1: aq. NaIO4 / 0.58 h / 0 - 20 °C
2: 11.4 g / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
3: Grubbs' catalyst / CH2Cl2 / 4 h / 24 °C
4: 8.3 g / 4 Angstroem molecular sieves; pyridinium dichromate; AcOH / CH2Cl2 / 12 h / 24 °C
View Scheme
参考文献
Jin, Yun H.; Liu, Peng; Wang, Jianing; Baker, Robert; Huggins, John; Chu, Chung K.
Journal of Organic Chemistry, 2003 , vol. 68, # 23 p. 9012 - 9018
反应条件
1: OsO4, N-methylmorpholine N-oxide
2: TsOH
3: H2 / Pd/C
4: 88 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH2Cl2
View Scheme
参考文献
Johnson, Carl R.; Esker, John L.; Zandt, Michael C. Van
Journal of Organic Chemistry, 1994 , vol. 59, # 20 p. 5854 - 5855
反应条件
1.1: 84 percent / tetrahydrofuran / -78 °C
2.1: Grubbs first generation catalyst / CH2Cl2 / 4 h / 20 °C
2.2: 87 percent / PCC / CH2Cl2 / 12 h
View Scheme
参考文献
Smith III, Amos B.; Han, Qiang; Breslin, Paul A. S.; Beauchamp, Gary K.
Organic Letters, 2005 , vol. 7, # 22 p. 5075 - 5078
反应条件
sodium methylate in methanol
3 h; Heating;
参考文献
Ohrui, Hiroshi; Konno, Masao; Meguro, Hiroshi
Agricultural and Biological Chemistry, 1987 , vol. 51, # 2 p. 625 - 626
反应条件
sodium periodate in tetrahydrofuran; water
T=55°C; 18 h; Yield given;
参考文献
Armstrong, Alan; Hayter, Barry R.
Tetrahedron Asymmetry, 1997 , vol. 8, # 10 p. 1677 - 1684
反应条件
1: 92 percent / CeCl3*7H2O; NaBH4 / methanol / 0.5 h / -78 °C
2: 43 percent / lipase PS, Pseudomonas sp. AMANO / various solvent(s) / 2 h / 20 °C
3: 95 percent / K2CO3 / methanol / 1.5 h / 20 °C
4: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C
5: 90 percent / NMO / aq. OsO4 / tetrahydrofuran / 72 h / 20 °C
6: 97 percent / PPTS / CH2Cl2 / 24 h / 20 °C
7: 98 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C
8: 96 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C
9: 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: 95 percent / PDC / CH2Cl2 / 20 °C
2: 92 percent / CeCl3*7H2O; NaBH4 / methanol / 0.5 h / -78 °C
3: 43 percent / lipase PS, Pseudomonas sp. AMANO / various solvent(s) / 2 h / 20 °C
4: 95 percent / K2CO3 / methanol / 1.5 h / 20 °C
5: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C
6: 90 percent / NMO / aq. OsO4 / tetrahydrofuran / 72 h / 20 °C
7: 97 percent / PPTS / CH2Cl2 / 24 h / 20 °C
8: 98 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C
9: 96 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C
10: 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: 100 percent / imidazole / dimethylformamide / 3 h / 20 °C
2: 90 percent / NMO / aq. OsO4 / tetrahydrofuran / 72 h / 20 °C
3: 97 percent / PPTS / CH2Cl2 / 24 h / 20 °C
4: 96 percent / H2 / 10 percent Pd/C; CHCl3 / ethyl acetate / 17 h / 20 °C
5: 97 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / 20 °C
6: 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
