Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

Ming Zhong Wang; Chuen Fai Ku; Tong Xu Si; Siu Wai Tsang; Xiao Meng Lv; Xiao Wan Li; Zheng Ming Li; Hongjie Zhang; Albert S C Chan

doi:10.1021/acs.jnatprod.7b00709

Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

Ming Zhong Wang^*
, Chuen Fai Ku
, Tong Xu Si
, Siu Wai Tsang
, Xiao Meng Lv
, Xiao Wan Li
, Zheng Ming Li
, Hongjie Zhang
, Albert S C Chan

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

12 Citations (Scopus)

Abstract

Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

Original language	English
Pages (from-to)	98-105
Number of pages	8
Journal	Journal of Natural Products
Volume	81
Issue number	1
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00709
Publication status	Published - 26 Jan 2018

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@article{77ec9ff1aec0480e9ee82b2946b39360,

title = "Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer",

abstract = "Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.",

author = "Wang, \{Ming Zhong\} and Ku, \{Chuen Fai\} and Si, \{Tong Xu\} and Tsang, \{Siu Wai\} and Lv, \{Xiao Meng\} and Li, \{Xiao Wan\} and Li, \{Zheng Ming\} and Hongjie Zhang and Chan, \{Albert S C\}",

note = "Funding Information: This work was financially supported by the Research Foundation for Advanced Talents (36000-18821101); Guangdong Natural Science Foundation (2017A030313751); the Fundamental Research Funds for the Central Universities (16ykpy33) of Sun Yat-sen University, Guangzhou, China; the Medical Scientific Research Foundation of Guangdong Province (A2016090); the Science and Technology Planning Project of Guangzhou City (201707010189), Hong Kong Scholars Program (XJ2013025), China; and the Interdisciplinary Research Matching Scheme (RC-IRMS/15-16/02) of Hong Kong Baptist University, Hong Kong SAR, China.",

year = "2018",

month = jan,

day = "26",

doi = "10.1021/acs.jnatprod.7b00709",

language = "English",

volume = "81",

pages = "98--105",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "1",

}

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T1 - Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

AU - Wang, Ming Zhong

AU - Ku, Chuen Fai

AU - Si, Tong Xu

AU - Tsang, Siu Wai

AU - Lv, Xiao Meng

AU - Li, Xiao Wan

AU - Li, Zheng Ming

AU - Zhang, Hongjie

AU - Chan, Albert S C

N1 - Funding Information: This work was financially supported by the Research Foundation for Advanced Talents (36000-18821101); Guangdong Natural Science Foundation (2017A030313751); the Fundamental Research Funds for the Central Universities (16ykpy33) of Sun Yat-sen University, Guangzhou, China; the Medical Scientific Research Foundation of Guangdong Province (A2016090); the Science and Technology Planning Project of Guangzhou City (201707010189), Hong Kong Scholars Program (XJ2013025), China; and the Interdisciplinary Research Matching Scheme (RC-IRMS/15-16/02) of Hong Kong Baptist University, Hong Kong SAR, China.

PY - 2018/1/26

Y1 - 2018/1/26

N2 - Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

AB - Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

UR - https://www.scopus.com/pages/publications/85041230128

U2 - 10.1021/acs.jnatprod.7b00709

DO - 10.1021/acs.jnatprod.7b00709

M3 - Journal article

C2 - 29281282

AN - SCOPUS:85041230128

SN - 0163-3864

VL - 81

SP - 98

EP - 105

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 1

ER -

Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

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