(3aR,4R,5R,6aS)-六氢-2-氧代-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[b]呋喃-5-基 [1,1’-联苯]-4-甲酸酯合成路线 （共 13 条）
反应条件
1: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 2: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 3: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 4: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
1: lithium triethylborohydride / tetrahydrofuran / 0.5 h 2: potassium carbonate / methanol; tetrahydrofuran / 2.5 h View Scheme
参考文献
Schaaf, Thomas K.; Bindra, Jasjit S.; Eggler, James F.; Plattner, Jacob J.; Nelson, A. James; et al.
Journal of Medicinal Chemistry, 1981 , vol. 24, # 11 p. 1353 - 1359
反应条件
1: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 2: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 3: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature 4: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
1: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 2: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 3: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 4: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h 6: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
1: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 2: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 3: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
N-ethyl-N,N-diisopropylamine; lithium chloride in acetonitrile
T=-15°C;
参考文献
Stjernschantz, Johan; Resul, Bahram
Patent: US2006/41016 A1, 2006 ;
Location in patent: Page/Page column 4 ;
反应条件
pyridine-SO3 complex; triethylamine in dichloromethane; dimethyl sulfoxide
T=-5 - 0°C; 1 h;
参考文献
Gutman, Arie; Rukhman, Igor; Tishin, Boris; Yudovich, Lev; Vilensky, Alexander; Pertsikov, Boris; Nisnevich, Gennady
Patent: US2009/163596 A1, 2009 ;
Location in patent: Page/Page column 13-14 ;
反应条件
1: in ethylene glycol dimethyl ether; dichloromethane
T=25 - 40°C;
2: With hydrogenchloride in ethylene glycol dimethyl ether; dichloromethane; water
T=18 - 20°C;
参考文献
MATRIX LABORATORIES LTD; KARUSALA, Nageswara Rao; CHAVHAN, Bhausaheb; POTLA, Murali Krishna; JEBARAJ, Rathinapandian,; GOSULA, Veera Venkata Satya Surya Appala Narasimha Tataj; GOSULA, Shiva Kumar; BURMA, Prabhakara Rao; DATTA, Debashish
Patent: WO2010/109476 A2, 2010 ;
Location in patent: Page/Page column 13 ;
反应条件
(Ph3P)AuNTf2; tert-butyl alcohol in water; butanone
T=20°C; Meyer-Schuster rearrangement; 23 h;
参考文献
Zanoni, Giuseppe; D'Alfonso, Alessandro; Porta, Alessio; Feliciani, Lazzaro; Nolan, Steven P.; Vidari, Giovanni
Tetrahedron, 2010 , vol. 66, # 38 p. 7472 - 7478
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h
2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h
View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
