NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2015, Vol. 27 ›› Issue (6): 945-951. doi: 10.16333/j.1001-6880.2015.06.002

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Total Synthesis of Four Isoflavones

WEI Tao,QIAO Jin-feng,WANG Ding,WEI Wei,HE Yun,ZHANG Zun-ting*   

  1. Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, School of Chemistry and Chemical Engineering,Shaanxi Normal University,Xi’an 710062,China
  • Online:2015-06-30 Published:2015-07-10

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Abstract: In this paper,a new method for the synthesis of 4 isoflavones,namely formononetin,daidzein,biochanin A and genistein was studied.Four isoflavones were synthesized starting from substituted 2-hydroxy-acetophenone via Negishi cross-coupling of substituted 3-iodochromones with arylzinc using NiCl2(PPh3)2 as catalyst.The method has a potential of industrialization,giving a higher atom utilization and good yield.The synthesis of the arylzinc reagent and the Negishi crosscoupling reactions were carried out at room temperature and did not need inert gas protection.The operation was easy and all process carried out under mild conditions.All of reagents were commonly used and friendly to environment.The structures of synthesized isoflavones were identified by IR, 1H NMR, 13C NMR and HR-MS.

Key words: isoflavones, NiCl2(PPh3)2, Negishi cross-coupling reaction, biochanin A

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