Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

Xiaowan Li, Tongxu Si, Chuen Fai KU, Hongjie Zhang, Mingzhong Wang*, Albert S C Chan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The total synthesis of the natural phytoalexin 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one (3) isolated from Eichhornia crassipes was accomplished in seven steps. The synthetic strategy included a Friedel-Crafts acylation and a Jacobsen-Katsuki epoxidation as the key reactions to obtain the target compound. Based on a comparison of the NMR data and a crystal structure of 3, the previously proposed structure of 2,5-dimethoxy-4-phenyl-benzoindenone (2) isolated from the same plant has been revised.

Original languageEnglish
Pages (from-to)183-189
Number of pages7
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume74
Issue number2
DOIs
Publication statusPublished - 25 Feb 2019

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • benzoindenone
  • NMR
  • structural revision
  • synthesis
  • X-ray structure determination

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