NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2010, Vol. 23 ›› Issue (6): 956-960.

• Article • Previous Articles     Next Articles

Synthesis of the Natural Product 5,6,7,3',4'-Pentamethoxyisoflavone

REN Wan-li1,CHEN  Rui2,JIN Ye2,ZHANG Tao2,LI Hong-qi2*   

  1. 1Medical School, Baoji Vocational and Technological College, Baoji 721006, China; 2Key Laboratory of Science & Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China

  • Received:2009-05-27 Online:2011-01-10 Published:2011-10-19
  • Supported by:

    This work was supported by Program for Changjiang Scholars and Innovative Research Team in University (No. IRT0526) and Shanghai Natural Science Foundation (No. 06ZR14001).

Abstract:

The natural product 5,6,7,3',4'-pentamethoxyisoflavone was synthesized by a 5-step synthetic protocol including esterification, Fries transformation, and Vilsmeier-Haack reaction with 3,4-dimethoxyphenylacetic acid and 3,4,5-trimethoxyphenol as the starting materials. The overall yield of the target compound was 76% based on 3,4,5-trimethoxyphenol. The structure of the natural isoflavone 5,6,7,3',4'-pentamethoxyisoflavone was confirmed by NMR and elemental analysis.

Key words: 5,6,7,3',4'-pentamethoxyisoflavone, 3,4,5-trimethoxyphenol, fries transformation, Vilsmeier-Haack reaction, synthesis