Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (5): 947.

• Articles • Previous Articles     Next Articles

Total Synthesis of the Dilignan threo-(±)-Diferuloysecoisolariciresinol

XIA Ya-Mu, WANG Wei, YANG Feng-Ke*, CHANG Liang   

  1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
  • Received:2009-07-16 Online:2010-05-10 Published:2010-05-10
  • Contact: YANG Feng-Ke. E-mail: YangFengK@qust.edu.cn
  • Supported by:

    山东省泰山学者基金(批准号: 2005011036)和青岛科技大学化学工程强化建设学科开放基金资助.

Abstract:

Threo-(±)-diferuloysecoisolariciresinol which belongs to dilignans, has been firstly isolated from the trunk of Machilus thunbergii and exhibits a strong bioactivity. A novel synthetic route to threo-(±)-diferuloysecoisolariciresinol using Vanillina as the starting materials was described. The method involved two Stobbe reactions to construct the skeleton of lignan(C6—C4—C6), followed by LiAlH4 reduction, hydrogenation to form meso- and threo-(±)-secoisolanciresinol. threo-(±)-Secoisolanciresinol confirmed by NMR, IR and HRMS was the synthetic key intermediate, and then condensated with ferulaic acid to give threo-(±)-diferuloysecoisolariciresinol. The synthesis was based on a unified synthetic strategy to obtain target products through 11 steps, with yield of 8%. The synthetic method has the advantages of easy availability of starting materials, simple operation. So it has considerable practical value.

Key words: Diferuloysecoisolariciresinol; Stobbe reaction; Dilignan; Total synthesis

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