Visible-Light Photocatalyzed Skeletal Rearrangement Enables the Synthesis of Highly Functionalized Xanthenes with Antitumor Activity
Shi-Lin Lin
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
These authors contributed equally.
Search for more papers by this authorFen Zhao
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
These authors contributed equally.
Search for more papers by this authorFen Wei
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
These authors contributed equally.
Search for more papers by this authorYing-Tong Shi
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorJing-Kai Wen
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorChao Yang
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorHao-Shuo Zhang
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorChuang-Chuang Li
Department of Chemistry, Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, 518055 P. R. China
Search for more papers by this authorCorresponding Author
Chang Liu
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorCorresponding Author
Wen-Cai Ye
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorCorresponding Author
Min-Jing Cheng
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorCorresponding Author
Lei Wang
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorShi-Lin Lin
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
These authors contributed equally.
Search for more papers by this authorFen Zhao
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
These authors contributed equally.
Search for more papers by this authorFen Wei
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
These authors contributed equally.
Search for more papers by this authorYing-Tong Shi
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorJing-Kai Wen
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorChao Yang
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorHao-Shuo Zhang
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorChuang-Chuang Li
Department of Chemistry, Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, 518055 P. R. China
Search for more papers by this authorCorresponding Author
Chang Liu
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorCorresponding Author
Wen-Cai Ye
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorCorresponding Author
Min-Jing Cheng
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorCorresponding Author
Lei Wang
State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou, 510632 P. R. China “.
Center for Bioactive Natural Molecules and Innovative Drugs, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China
Search for more papers by this authorAbstract
Highly functionalized xanthenes possess an impressive range of bioactivities and daunting synthetic challenge due to their unique ring systems and stereocenters. Here, we report an unprecedented ketyl radicals-induced skeletal rearrangement reaction of spirodihydrobenzofurans, enabled by zero-valent iron as reducing agents via photoredox catalysis, facilitating the facile preparation of various highly functionalized xanthenes. The features of this protocol include high chemo- and regioselectivity, exceptionally mild conditions, a broad substrate scope, scalability to gram-scale quantities, and consistent delivery of good to excellent yields. Mechanistic studies rationalize the function of this zero-valent iron-based reactivity in radical generation. Notably, this reaction was applied to the first asymmetric total synthesis of the complex polycyclic xanthene ent-myrtucomvalones E−F. Moreover, this work led to the discovery of an agent with highly effective antiosteosarcoma activity in vitro and in vivo, potentially paving the way for the development of new xanthene-based candidates for osteosarcoma treatment.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the Supporting Information of this article.
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