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