Construction of 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via ternary catalysis

Mengchu Zhang; Tianyuan  Zhang; Sifan Yu; Huang Qiu; Abdullah Yusuf; Xinfang Xu; Yu  Qian; Wenhao Hu

doi:10.1039/D3SC03452F

Construction of 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via ternary catalysis

Mengchu Zhang
, Tianyuan Zhang
, Sifan Yu
, Huang Qiu
, Abdullah Yusuf
, Xinfang Xu
, Yu Qian^*
, Wenhao Hu^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

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

7 Citations (Scopus)

Abstract

4-Hydroxycoumarin derivatives represent one of the most important scaffolds in biologically active substances, pharmaceuticals and functional materials. Herein, we describe an efficient Pd/amine/Brønsted acid ternary-catalytic multicomponent reaction for the rapid construction of substituted 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via convergent assembly of two in situ generated active intermediates. Furthermore, the late-stage transformations of coumarin derivatives and their in vitro trial of antitumor activity successfully demonstrated the potential utilities of the products as platform molecules.

Original language	English
Pages (from-to)	11850-11857
Number of pages	8
Journal	Chemical Science
Volume	42
DOIs	https://doi.org/10.1039/D3SC03452F
Publication status	Published - 14 Nov 2023

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10.1039/D3SC03452FLicence: CC BY-NC

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@article{54eb110126c24ba8bf37d2df8b5c7b63,

title = "Construction of 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via ternary catalysis",

abstract = "4-Hydroxycoumarin derivatives represent one of the most important scaffolds in biologically active substances, pharmaceuticals and functional materials. Herein, we describe an efficient Pd/amine/Br{\o}nsted acid ternary-catalytic multicomponent reaction for the rapid construction of substituted 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via convergent assembly of two in situ generated active intermediates. Furthermore, the late-stage transformations of coumarin derivatives and their in vitro trial of antitumor activity successfully demonstrated the potential utilities of the products as platform molecules.",

author = "Mengchu Zhang and Tianyuan Zhang and Sifan Yu and Huang Qiu and Abdullah Yusuf and Xinfang Xu and Yu Qian and Wenhao Hu",

note = "Support for this research from the National Natural Science Foundation of China (92056201, 22171294, 81973176, 22001268), the Natural Science Foundation of Guangdong Province, China (2021A1515010401), Key-Area Research and Development Program of Guangdong Province (2022B1111050003), Guangdong Provincial Key Laboratory of Construction Foundation (2023B1212060022), Guangdong Natural Science Fund (2023A1515011486) and the Key Laboratory Open Project of Xinjiang Uygur Autonomous Region (2021D04018) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2023 The Author(s). Published by the Royal Society of Chemistry",

year = "2023",

month = nov,

day = "14",

doi = "10.1039/D3SC03452F",

language = "English",

volume = "42",

pages = "11850--11857",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Construction of 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via ternary catalysis

AU - Zhang, Mengchu

AU - Zhang, Tianyuan

AU - Yu, Sifan

AU - Qiu, Huang

AU - Yusuf, Abdullah

AU - Xu, Xinfang

AU - Qian, Yu

AU - Hu, Wenhao

N1 - Support for this research from the National Natural Science Foundation of China (92056201, 22171294, 81973176, 22001268), the Natural Science Foundation of Guangdong Province, China (2021A1515010401), Key-Area Research and Development Program of Guangdong Province (2022B1111050003), Guangdong Provincial Key Laboratory of Construction Foundation (2023B1212060022), Guangdong Natural Science Fund (2023A1515011486) and the Key Laboratory Open Project of Xinjiang Uygur Autonomous Region (2021D04018) is gratefully acknowledged. Publisher Copyright: © 2023 The Author(s). Published by the Royal Society of Chemistry

PY - 2023/11/14

Y1 - 2023/11/14

N2 - 4-Hydroxycoumarin derivatives represent one of the most important scaffolds in biologically active substances, pharmaceuticals and functional materials. Herein, we describe an efficient Pd/amine/Brønsted acid ternary-catalytic multicomponent reaction for the rapid construction of substituted 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via convergent assembly of two in situ generated active intermediates. Furthermore, the late-stage transformations of coumarin derivatives and their in vitro trial of antitumor activity successfully demonstrated the potential utilities of the products as platform molecules.

AB - 4-Hydroxycoumarin derivatives represent one of the most important scaffolds in biologically active substances, pharmaceuticals and functional materials. Herein, we describe an efficient Pd/amine/Brønsted acid ternary-catalytic multicomponent reaction for the rapid construction of substituted 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via convergent assembly of two in situ generated active intermediates. Furthermore, the late-stage transformations of coumarin derivatives and their in vitro trial of antitumor activity successfully demonstrated the potential utilities of the products as platform molecules.

UR - https://pubs.rsc.org/en/content/articlelanding/2023/sc/d3sc03452f

U2 - 10.1039/D3SC03452F

DO - 10.1039/D3SC03452F

M3 - Journal article

SN - 2041-6520

VL - 42

SP - 11850

EP - 11857

JO - Chemical Science

JF - Chemical Science

ER -

Construction of 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters via ternary catalysis

Abstract

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