(+)-(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: 75 percent / dicyclohexylcarbodiimide; CF3CO2H; pyridine / DMSO / toluene / 10 h / 20 °C
2: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C
3: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
4: aq. NaIO4 / 0.58 h / 0 - 20 °C
5: 11.4 g / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
6: Grubbs' catalyst / CH2Cl2 / 4 h / 24 °C
7: 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: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C
2: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
3: aq. NaIO4 / 0.58 h / 0 - 20 °C
4: 11.4 g / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
5: Grubbs' catalyst / CH2Cl2 / 4 h / 24 °C
6: 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: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
2: aq. NaIO4 / 0.58 h / 0 - 20 °C
3: 11.4 g / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
4: Grubbs' catalyst / CH2Cl2 / 4 h / 24 °C
5: 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: 99 percent / p-toluenesulfonic acid hydrate / 60 h
2: 99 percent / KOH / methanol / 0.5 h
3: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h
4: 1.) n-BuLi, triphenylmethane / 1.) hexane-THF, 0 deg C, 15 min; 2.) hexane-THF, -78 deg C,15 min
5: 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: With water; iodine in tetrahydrofuran
T=20°C; 0.0833333 h;
2: With zinc in benzene
Reformatsky reaction; 2.5 h; Reflux;
参考文献
Ivanova, Nadezhda A.; Valiullina, Zuleykha R.; Akhmetdinova, Natal'ya P.; Miftakhov, Mansur S.
Tetrahedron Letters, 2008 , vol. 49, # 43 p. 6179 - 6181
反应条件
acetic acid
T=60°C; Elimination; 96 h;
参考文献
Nakashima, Hiromi; Sato, Masayuki; Taniguchi, Takahiko; Ogasawara, Kunio
Synthesis, 2000 , # 6 p. 817 - 823
反应条件
acetic acid
T=60°C; Elimination; 96 h;
参考文献
Nakashima, Hiromi; Sato, Masayuki; Taniguchi, Takahiko; Ogasawara, Kunio
Synthesis, 2000 , # 6 p. 817 - 823
反应条件
1: With N-bromosuccinmide; water in tetrahydrofuran
T=20°C; 0.0833333 h;
2: With sodium iodide; zinc in tetrahydrofuran
2 h; Reflux;
参考文献
Ivanova, Nadezhda A.; Valiullina, Zuleykha R.; Akhmetdinova, Natal'ya P.; Miftakhov, Mansur S.
Tetrahedron Letters, 2008 , vol. 49, # 43 p. 6179 - 6181
反应条件
perchloric acid in acetone
2 h; bath temperature 70 deg C;
参考文献
Flann, Christopher J.; Mash, Eugene A.
Synthetic Communications, 1988 , vol. 18, # 4 p. 391 - 402
反应条件
pyridine; molecular sieve; pyridinium chlorochromate in dichloromethane
参考文献
Biadatti, Thibaud; Esker, John L.; Johnson, Carl R.
Tetrahedron Asymmetry, 1996 , vol. 7, # 8 p. 2313 - 2320
