Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (09): 1605-1610. Previous Articles     Next Articles

Original Articles


汪秋安*; 张卓佳 ; 张春香 ; 范华芳   

  1. (湖南大学化学化工学院 长沙 410082)
  • 收稿日期:2007-09-14 修回日期:2007-12-07 发布日期:2008-09-20
  • 通讯作者: 汪秋安

Synthesis of 8-5’ Neolignan Compounds

WANG, Qiu-An*; ZHANG, Zhuo-Jia; ZHANG, Chun-Xiang ; FAN, Hua-Fang   

  1. (College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
  • Received:2007-09-14 Revised:2007-12-07 Published:2008-09-20
  • Contact: WANG, Qiu-An

Eleven 8-5’ neolignan compounds 3a~9b have been synthesized via reactions of dihydrobenzofuran compounds 1 and 2 with dry K2CO3 or 10% NaOH (aq.) under distinct conditions. 1a and 1b were synthesized from methyl 4-hydroxy cinnamate and methyl ferulate respectively by Ag2O-catalyzed biomi-metic oxidative coupling reaction while 2a and 2b were obtained through methylation of 1a and 1b, respec-tivly Synthesis of compounds 3a~9b not only achieved transformation successfully from dihydrobenzofuran neolignans to 8-5’ neolignans, but also offered a new method for the synthesis of stilbenoids. The effect of 8-electron-withdrawing substituents such as COOCH3 group made transformation smoothly from dihydrobenzofuren neolignans to 8-5’ neolignan compounds. All of these synthesized compounds have been confirmed by MS, IR, 1HNMR and 13CNMR techniques.

Key words: neolignan, 8-5’ neolignan compound, synthesis, stilbenoid, dihydrobenzofuran