(+)-Calanolide B 合成路线 (共 8 条)
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反应条件
142632-32-4 (10R,11S,12S)-11,12-二氢-12-羟基-6,6,10,11-四甲基-4-丙基-2H,6H,10H-苯并(1,2-b:3,4-b':5,6-b'')三吡喃-2-酮
反应条件
1: With lithium tri-t-butoxyaluminum hydride in tetrahydrofuran T=-15 - 20°C; 15.5 h; 2: With hydrogenchloride in tetrahydrofuran; water pH=3;
参考文献
Kuraray Co., Ltd.; SAGAMI CHEMICAL RESEARCH CENTER
Patent: EP1352907 A1, 2003 ;
Location in patent: Page/Page column 20 ;
反应条件
acetic acid in tetrahydrofuran; ethyl acetate
参考文献
The University of Tennessee Research Corporation
Patent: US5608085 A1, 1997 ;
反应条件
tetrabutyl ammonium fluoride in tetrahydrofuran
参考文献
Deshpande, Prashant P.; Tagliaferri, Frank; Victory, Samuel F.; Yan, Shija; Baker, David C.
Journal of Organic Chemistry, 1995 , vol. 60, # 10 p. 2964 - 2965
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反应条件
142632-32-4 (10R,11S,12S)-11,12-二氢-12-羟基-6,6,10,11-四甲基-4-丙基-2H,6H,10H-苯并(1,2-b:3,4-b':5,6-b'')三吡喃-2-酮
反应条件
1: With propionic acid; 3,4,5-trimethoxyphenylboronic acid in toluene 1.5 h; Heating; 2: With lithium aluminium tetrahydride; tert-butyl alcohol in tetrahydrofuran
参考文献
Sekino, Etsuko; Kumamoto, Takuya; Tanaka, Tomohiro; Ikeda, Tomoko; Ishikawa, Tsutomu
Journal of Organic Chemistry, 2004 , vol. 69, # 8 p. 2760 - 2767
反应条件
1.1: 77 percent / MgI2; K2CO3 / benzene / 360 h / Heating 2.1: phenylboronic acid; propionic acid / toluene / 1.5 h / Heating 2.2: 12 percent / LiAlH4; tert-butyl alcohol / tetrahydrofuran View Scheme
参考文献
Sekino, Etsuko; Kumamoto, Takuya; Tanaka, Tomohiro; Ikeda, Tomoko; Ishikawa, Tsutomu
Journal of Organic Chemistry, 2004 , vol. 69, # 8 p. 2760 - 2767
反应条件
1: 1.) LDA, 2.) TiCl4 3: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 5 h / Ambient temperature; also 6,6-dimethyl-9-hydroxy-10<2(R)-methyl-3(R)-hydroxybutyro>-4-propyl-2H,6H-benzo<1,2-b:3,4-b'>dipyran-2-one 4: 1.) CeCl3*7H2O, triphenylphosphine oxide, 2.) NaBH4 / 1.) EtOH, RT, 1 h, 2.) EtOH, -30 deg C, 5.5 h View Scheme
参考文献
Khilevich, Albert; Mar, Aye; Flavin, Michael T.; Rizzo, John D.; Lin, Lin; Dzekhtser, Sergey; Brankovic, Darko; Zhang, Heping; Chen, Wei; Liao, Shuyuan; Zembower, David E.; Xu, Ze-Qi
Tetrahedron Asymmetry, 1996 , vol. 7, # 11 p. 3315 - 3326
反应条件
1: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 5 h / Ambient temperature; also 6,6-dimethyl-9-hydroxy-10<2(R)-methyl-3(R)-hydroxybutyro>-4-propyl-2H,6H-benzo<1,2-b:3,4-b'>dipyran-2-one 2: 1.) CeCl3*7H2O, triphenylphosphine oxide, 2.) NaBH4 / 1.) EtOH, RT, 1 h, 2.) EtOH, -30 deg C, 5.5 h View Scheme
参考文献
Khilevich, Albert; Mar, Aye; Flavin, Michael T.; Rizzo, John D.; Lin, Lin; Dzekhtser, Sergey; Brankovic, Darko; Zhang, Heping; Chen, Wei; Liao, Shuyuan; Zembower, David E.; Xu, Ze-Qi
Tetrahedron Asymmetry, 1996 , vol. 7, # 11 p. 3315 - 3326
反应条件
1: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 5 h / Ambient temperature 2: 1.) CeCl3*7H2O, triphenylphosphine oxide, 2.) NaBH4 / 1.) EtOH, RT, 1 h, 2.) EtOH, -30 deg C, 5.5 h View Scheme
参考文献
Khilevich, Albert; Mar, Aye; Flavin, Michael T.; Rizzo, John D.; Lin, Lin; Dzekhtser, Sergey; Brankovic, Darko; Zhang, Heping; Chen, Wei; Liao, Shuyuan; Zembower, David E.; Xu, Ze-Qi
Tetrahedron Asymmetry, 1996 , vol. 7, # 11 p. 3315 - 3326