(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓合成路线 （共 13 条）
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
potassium carbonate in methanol
T=25°C; 0.5 h;
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
potassium carbonate in methanol
T=25°C; 0.5 h;
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
1.1: BF3*OEt2 / CH2Cl2 / 0 °C
1.2: 50 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
2.1: 80 percent / RuCH=RuCH[(Mes)NCH2CH2N(Mes)](PCy3)Cl2 / CH2Cl2 / 17 h
3.1: aq. NaIO4 / methanol / 0.33 h / 25 °C
3.2: 75 percent / NaHB4 / methanol / 1 h / 0 °C
4.1: 85 percent / pyridine / CH2Cl2 / 12 h / 25 °C
5.1: 80 percent / LiBr / hexamethylphosphoric acid triamide / 20 h / 50 °C
6.1: 78 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.5 h / 25 °C
7.1: 95 percent / K2CO3 / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
1.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
2.1: NaHMDS / tetrahydrofuran / 1 h / 25 °C
2.2: 60 percent / tetrahydrofuran / 12 h
3.1: BF3*OEt2 / CH2Cl2 / 0 °C
3.2: 50 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
4.1: 80 percent / RuCH=RuCH[(Mes)NCH2CH2N(Mes)](PCy3)Cl2 / CH2Cl2 / 17 h
5.1: aq. NaIO4 / methanol / 0.33 h / 25 °C
5.2: 75 percent / NaHB4 / methanol / 1 h / 0 °C
6.1: 85 percent / pyridine / CH2Cl2 / 12 h / 25 °C
7.1: 80 percent / LiBr / hexamethylphosphoric acid triamide / 20 h / 50 °C
8.1: 78 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.5 h / 25 °C
9.1: 95 percent / K2CO3 / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
Rhinocladiella sp. K-001
T=26°C; 504 h;
参考文献
Koshimura, Masahiro; Utsukihara, Takamitsu; Kawamoto, Mai; Saito, Michihiko; Horiuchi, C. Akira; Kuniyoshi, Masayuki
Phytochemistry, 2009 , vol. 70, # 17-18 p. 2023 - 2026
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
1: 85 percent / pyridine / CH2Cl2 / 12 h / 25 °C
2: 80 percent / LiBr / hexamethylphosphoric acid triamide / 20 h / 50 °C
3: 78 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.5 h / 25 °C
4: 95 percent / K2CO3 / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
1: 80 percent / LiBr / hexamethylphosphoric acid triamide / 20 h / 50 °C
2: 78 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.5 h / 25 °C
3: 95 percent / K2CO3 / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
1: 78 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.5 h / 25 °C
2: 95 percent / K2CO3 / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Cooladouros, Elias A.; Vidali, Veroniki P.
Chemistry - A European Journal, 2004 , vol. 10, # 15 p. 3822 - 3835
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
2: 50 percent aq. K2CO3 / methanol / 0.25 h / Ambient temperature
View Scheme
参考文献
Tanaka, Akira; Suzuki, Masanobu; Yamashita, Kyohei
Agricultural and Biological Chemistry, 1986 , vol. 50, # 4 p. 1069 - 1072
→
77249-86-6(3aR,4aS,7S,8aS)-7-溴-1,3,3a,4a,5,6,7,8,8a,9-十氢-4a,8,8-三甲基呋喃并[3,4-b][1]苯并氧杂卓
反应条件
1: pyridine
2: LiBr.H2O / dimethylformamide / 2.5 h / 80 - 90 °C
4: 50 percent aq. K2CO3 / methanol / 0.25 h / Ambient temperature
View Scheme
参考文献
Tanaka, Akira; Suzuki, Masanobu; Yamashita, Kyohei
Agricultural and Biological Chemistry, 1986 , vol. 50, # 4 p. 1069 - 1072
