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

doi:10.1515/znb-2018-0181

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 journal › Journal article › peer-review

2 Citations (Scopus)

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 language	English
Pages (from-to)	183-189
Number of pages	7
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	74
Issue number	2
Early online date	6 Jan 2019
DOIs	https://doi.org/10.1515/znb-2018-0181
Publication status	Published - 25 Feb 2019

User-Defined Keywords

benzoindenone
NMR
structural revision
synthesis
X-ray structure determination

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

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.",

keywords = "benzoindenone, NMR, structural revision, synthesis, X-ray structure determination",

author = "Xiaowan Li and Tongxu Si and KU, \{Chuen Fai\} and Hongjie Zhang and Mingzhong Wang and Chan, \{Albert S C\}",

note = "Funding Information: Acknowledgment: This work was financially supported by the Research Foundation for Advanced Talents (36000-18821101), Guangdong Natural Science Foundation (2017A030313751), The Science and Technology Planning Project of Guangzhou City (201707010189), The China Postdoctoral Science Foundation (2018M640942), and the Interdisciplinary Research Matching Scheme (RC-IRMS/15-16/02) of Hong Kong Baptist University, Hong Kong SAR, China.",

year = "2019",

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doi = "10.1515/znb-2018-0181",

language = "English",

volume = "74",

pages = "183--189",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

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T1 - Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

AU - Li, Xiaowan

AU - Si, Tongxu

AU - KU, Chuen Fai

AU - Zhang, Hongjie

AU - Wang, Mingzhong

AU - Chan, Albert S C

N1 - Funding Information: Acknowledgment: This work was financially supported by the Research Foundation for Advanced Talents (36000-18821101), Guangdong Natural Science Foundation (2017A030313751), The Science and Technology Planning Project of Guangzhou City (201707010189), The China Postdoctoral Science Foundation (2018M640942), and the Interdisciplinary Research Matching Scheme (RC-IRMS/15-16/02) of Hong Kong Baptist University, Hong Kong SAR, China.

PY - 2019/2/25

Y1 - 2019/2/25

N2 - 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.

AB - 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.

KW - benzoindenone

KW - NMR

KW - structural revision

KW - synthesis

KW - X-ray structure determination

UR - https://www.scopus.com/pages/publications/85060027790

U2 - 10.1515/znb-2018-0181

DO - 10.1515/znb-2018-0181

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AN - SCOPUS:85060027790

SN - 0932-0776

VL - 74

SP - 183

EP - 189

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 2

ER -

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

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