[3aR(3aα,4α,5β,6aα)]-(-)-5-(苯甲酰氧基)六氢-2-氧代-2H-环戊并[b]呋喃-4-甲醛合成路线 （共 14 条）
反应条件
Dess-Martin periodane in dichloromethane T=0 - 20°C; 1 h;
参考文献
Fleming, Ian; Winter, Stephen B. D.
Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2687 - 2700
反应条件
sulfur trioxide pyridine complex Inert atmosphere;
参考文献
Ohta, Chisa; Kuwabe, Shin-Itsu; Shiraishi, Tai; Shinohara, Ikuo; Araki, Hiroshi; Sakuyama, Shigeru; Makihara, Takayuki; Kawanaka, Yasufumi; Ohuchida, Shuichi; Takuya, Seko
Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8298 - 8308
反应条件
1: (2-oxoheptyl)phosphonic acid dimethyl ester With lithium hydroxide in tert-butyl methyl ether T=20°C; 1 h; 2: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde in tert-butyl methyl ether; water T=20°C; 1 h;
参考文献
R-TECH UENO, LTD.
Patent: US2007/244333 A1, 2007 ;
Location in patent: Page/Page column 14-15 ;
反应条件
sodium hexamethyldisilazane in tetrahydrofuran T=-78 - 20°C; Inert atmosphere;
参考文献
Patel, Pranav; Lee, Gue-Jae; Kim, Seongjin; Grant, Gail E.; Powell, William S.; Rokach, Joshua
Journal of Organic Chemistry, 2008 , vol. 73, # 18 p. 7213 - 7218
反应条件
1: dimethyl (2-oxoheptyl)phosphonate With sodium hydride in tetrahydrofuran T=0 - 20°C; 2: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde in tetrahydrofuran T=20°C; 1.5 h;
参考文献
Zanoni, Giuseppe; Porta, Alessio; de Toma, Quintino; Castronovo, Francesca; Vidari, Giovanni
Journal of Organic Chemistry, 2003 , vol. 68, # 16 p. 6437 - 6439
反应条件
sodium hexamethyldisilazane in tetrahydrofuran T=-78 - 20°C; Horner-Emmons reaction;
参考文献
Kim, Seongjin; Bellone, Sophie; Maxey, Kirk M.; Powell, William S.; Lee, Gue-Jae; Rokach, Joshua
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 7 p. 1873 - 1876
反应条件
lithium hexamethyldisilazane in tetrahydrofuran T=-78 - 20°C; Horner-Emmons reaction;
参考文献
Kim, Seongjin; Bellone, Sophie; Maxey, Kirk M.; Powell, William S.; Lee, Gue-Jae; Rokach, Joshua
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 7 p. 1873 - 1876
反应条件
sodium tetrahydroborate in methanol; dichloromethane T=0°C; 0.416667 h;
参考文献
Alcon Laboratories, Inc.
Patent: US6353000 B1, 2002 ;
Location in patent: Page column 10 ;
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / |Inert atmosphere 1.2: 0.5 h / 26 °C / |Inert atmosphere 1.3: 20 h / 25 - 45 °C 2.1: carbon / ethyl acetate / 2 h / 25 - 40 °C 2.2: 20 - 25 °C / 1034.32 - 1292.9 Torr / |Inert atmosphere 3.1: potassium carbonate / methanol / 17 h / 25 - 35 °C / |Inert atmosphere 4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.17 h / 25 °C / |Inert atmosphere 4.2: 16 h / 25 °C 5.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 2 h / -15 - -10 °C / |Inert atmosphere 6.1: diisobutylaluminium hydride / toluene / 2 h / -65 - 70 °C 7.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 - 5 °C / |Inert atmosphere 7.2: 2 h / 0 - 5 °C 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 19 - 25 °C / |Inert atmosphere 8.2: 18 h / 20 - 25 °C 9.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 2 h / 6 - 12 °C / |Inert atmosphere 10.1: hydrogenchloride / acetonitrile; water / 4 h / 13 - 20 °C 11.1: carbon / ethyl acetate / 2 h / 20 °C 11.2: 1.5 h / 17 - 25 °C / 2250.23 Torr View Scheme
参考文献
Jackson, Mark; Dahanukar, Vilas Hareshwar; Joseph, Suju Chuttippari; Eda, Vishnu Vardhana Verma Reddy; Ramdas, Sandip Khobare
Patent: US2013/184476 A1, 2013 ;
反应条件
1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5: NaN(SiMe3)2 / tetrahydrofuran / 3 h / 0 °C View Scheme
参考文献
DR.REDDYS LABORATORIES LIMITED; JACKSON, Mark P
Patent: WO2013/118058 A1, 2013 ;
