Open Access
,
volume 10
Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans
Kai Wei
1, 2
,
Yucui Sun
1
,
Yiren Xu
1
,
Wen Hu
1
,
Ying Ma
1
,
Yi Lu
1
,
Wen Chen
1
,
Hongbin Zhang
1
1
Key Laboratory of Medicinal Chemistry for Natural Resource, China
|
2
Henan Engineering Research Center of Funiu Mountain’s Medical Resources Utilization and Molecular Medicine, China
|
Publication type: Journal Article
Publication date: 2022-12-22
scimago Q1
wos Q2
SJR: 0.830
CiteScore: 8.4
Impact factor: 4.2
ISSN: 22962646
PubMed ID:
36618865
General Chemistry
Abstract
Lignans are widely present in traditional medicinal plants. Many natural arylnaphthalene lactone lignans (NALLs) isolated from the genera Justicia, Haplophyllum, and Phyllanthus possess interesting biological activities. Herein, we report a general strategy for the total synthesis of this kind of lignans. Features of this new approach are an aryl–alkyl Suzuki cross-coupling to introduce the dioxinone unit, a cation-induced cyclization to construct the aryl dihydronaphthalene, and base-mediated oxidative aromatization to furnish the arylnaphthalene core. By incorporating these key transformations, the total syntheses of justicidins B and E and taiwanin C covered type I and type II NALLs were accomplished.
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Wei K. et al. Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans // Frontiers in Chemistry. 2022. Vol. 10.
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Wei K., Sun Y., Xu Y., Hu W., Ma Y., Lu Y., Chen W., Zhang H. Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans // Frontiers in Chemistry. 2022. Vol. 10.
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TY - JOUR
DO - 10.3389/fchem.2022.1103554
UR - https://doi.org/10.3389/fchem.2022.1103554
TI - Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans
T2 - Frontiers in Chemistry
AU - Wei, Kai
AU - Sun, Yucui
AU - Xu, Yiren
AU - Hu, Wen
AU - Ma, Ying
AU - Lu, Yi
AU - Chen, Wen
AU - Zhang, Hongbin
PY - 2022
DA - 2022/12/22
PB - Frontiers Media S.A.
VL - 10
PMID - 36618865
SN - 2296-2646
ER -
Cite this
BibTex (up to 50 authors)
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@article{2022_Wei,
author = {Kai Wei and Yucui Sun and Yiren Xu and Wen Hu and Ying Ma and Yi Lu and Wen Chen and Hongbin Zhang},
title = {Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans},
journal = {Frontiers in Chemistry},
year = {2022},
volume = {10},
publisher = {Frontiers Media S.A.},
month = {dec},
url = {https://doi.org/10.3389/fchem.2022.1103554},
doi = {10.3389/fchem.2022.1103554}
}