CRCU

Chemical Research in Chinese Universities ›› 2011, Vol. 27 ›› Issue (6): 949-954.

• Articles • Previous Articles     Next Articles

Synthesis of Naturally Occurring Neolignans Demethylnitidanin, Herpetol and Salvinal as well as Their Glycosyl Derivatives

WU Zheng, LIANG Zhi-ying, LI Wei, REN Ying-mei and WANG Qiu-an*   

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
  • Received:2011-01-21 Revised:2011-03-30 Online:2011-11-25 Published:2011-11-07
  • Contact: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
  • Supported by:

    Supported by the Personal Training Funds in National Basic Science of China(No.J0830415).

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Abstract: Three neolignans, (±)-demethylnitidanin(1), herpetol(2) and salvinal(3) were synthesized from methyl 4,5-dihydroxy-3-methoxy cinnamate or methyl 4-hydroxy-3-methoxy cinnamate with Ag2O-catalyzed biomimetic oxidative coupling as the key step of the synthetic route. Five novel benzofuran neolignan-4'-O-β-D-glycosides(4―8) were achieved by the glycosylation reactions of benzofuran neolignans 2, 3 and 15. The structures of all the compounds synthesized were determined by MS, 1H NMR and IR spectra. (±)-Demethylnitidanin(1) and herpetol(2) were the first synthesized and the synthesis of salvinal(3) was efficiently improved by the new synthetic routes.

Key words: Neolignan, (±)-Demethylnitidanin, Herpetol, Salvinal, Glycosylation