Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (7): 1342.

• Articles • Previous Articles     Next Articles

Modified Total Synthesis of Verbenachalcone

ZHANG Ying-Peng*, CHEN Yu-Tao, YANG Yun-Shang, GUAN Xiao   

  1. Institute of Organic & Pharmaceutical Chemistry, School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou 730050, China
  • Received:2009-11-30 Online:2010-07-10 Published:2010-07-10
  • Contact: ZHANG Ying-Peng. E-mail: yingpengzhang@126.com
  • Supported by:

    甘肃省自然科学基金(批准号: 3ZS062-B25-017)资助.

Abstract:

A new and simple method for synthesis of verbenachalcone(1) was reported. A method for reverse synthesis design was adopted to two synthetic fragments, compound 4 and compound 6. Then the two fragments were combined together, starting from p-hydroxybenzaldehyde(2) through acetylation, bromination, Ullmann reaction, methoxymethylation, aldol condensation, deprotection, catalytic hydrogenation seven steps to target compound, with total yield of 39.1%. The key steps were the Ullmann reaction of 3-bromo-4-hydroxybenzaldehyde(3) with vanilline. The chemical structures of the key intermediate and final target product were verified by 1H NMR, 13C NMR and ESI-MS.

Key words: Verbenachalcone; Ullmann reaction; Total synthesis; Aldol condensation

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