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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/126/03/0813-0820

    • Keywords

       

      Boehmenan; dihydrobenzofuran neolignan; dilignan; biomimetic oxidative coupling; ring-opening reaction mechanism.

    • Abstract

       

      The first total synthesis of dilignan Boehmenan has been achieved. A biomimetic oxidative coupling of the ferulic acid methyl ester in the presence of silver oxide is the crucial step in the synthesis sequence, generating the dihydrobenzofuran skeleton. Hydroxyl group was protected with DHP and reducted with LiAlH4 to afford the intermediate diol. The diol was condensated with the derivative of ferulic acid, then removed the protecting groups, to get Boehmenan. Meanwhile, a study on the ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.

    • Author Affiliations

       

      Yamu Xia1 Xiaoli Dai1 Haixin Liu1 Chen Chai2

      1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, People’s Republic of China
      2. The first Affiliated Hospital of Lanzhou University, Gansu 730000, People’s Republic of China

    • Dates

       
      Published
      May 2014
      Manuscript received
      27 April 2013
      Manuscript revised
      29 July 2013
      Accepted
      14 November 2013

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