Enantioselective total syntheses of six natural and two proposed meroterpenoids from Psoralea corylifolia

被引:6
作者
Chen, Xiao-Wei [1 ]
Hou, Zi-Chao [1 ]
Chen, Chi [1 ]
Zhang, Ling-Hui [1 ]
Chen, Meng-En [1 ]
Zhang, Fu-Min [1 ,2 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug Dev, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
关键词
CHEMICAL-CONSTITUENTS; IRON(III) CHLORIDE; CARBONYL-COMPOUNDS; CONSTRUCTION; ECONOMY; CONDENSATION; DERIVATIVES; ARYLATION; KETONES; ARENES;
D O I
10.1039/d3sc00582h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first enantioselective total syntheses of six natural and two proposed meroterpenoids isolated from Psoralea corylifolia have been achieved in 7-9 steps from 2-methylcyclohexanone. The current synthetic approaches feature a high level of synthetic flexibility, stereodivergent fashion and short synthetic route, thereby providing a potential platform for the preparation of numerous this-type meroterpenoids and their pseudo-natural products.
引用
收藏
页码:5699 / 5704
页数:6
相关论文
共 97 条
[1]   Psoralea corylifolia L: Ethnobotanical, biological, and chemical aspects: A review [J].
Alam, Fiaz ;
Khan, Gul Nawaz ;
Bin Asad, Muhammad Hassham Hassan .
PHYTOTHERAPY RESEARCH, 2018, 32 (04) :597-615
[2]   Carbonyl-Olefin Metathesis [J].
Albright, Haley ;
Davis, Ashlee J. ;
Gomez-Lopez, Jessica L. ;
Vonesh, Hannah L. ;
Quach, Phong K. ;
Lambert, Tristan H. ;
Schindler, Corinna S. .
CHEMICAL REVIEWS, 2021, 121 (15) :9359-9406
[3]   Enantioselective Total Synthesis of (+)-Aberrarone [J].
Amberg, Willi M. ;
Carreira, Erick M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (34) :15475-15479
[4]   Bioactive terpenoids derived from plant endophytic fungi: An updated review (2011-2020) [J].
Amirzakariya, Bahman Zamani ;
Shakeri, Abolfazl .
PHYTOCHEMISTRY, 2022, 197
[5]   Transition-metal-free α-arylation of nitroketones with diaryliodonium salts for the synthesis of tertiary α-aryl, α-nitro ketones [J].
An, Yang ;
Zhang, Xiao-Ming ;
Li, Ze-Yu ;
Xiong, Wen-Hui ;
Yu, Run-Dong ;
Zhang, Fu-Min .
CHEMICAL COMMUNICATIONS, 2019, 55 (01) :119-122
[6]   Catalytic Enantioselective Pictet-Spengler Reaction of α-Ketoamides Catalyzed by a Single H-Bond Donor Organocatalyst [J].
Andres, Remi ;
Wang, Qian ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (19)
[7]   Multiple Catalytic C-H Bond Functionalization for Natural Product Synthesis [J].
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (41) :17798-17809
[8]   Transition-Metal-Free Site-Selective γ-C(sp2)-H Monoiodination of Arenes Directed by an Aliphatic Keto Group [J].
Bian, Hong-Li ;
Tang, Shi-Zhong ;
Chen, Meng-En ;
Zhang, Xiao-Ming ;
Lv, Jian-Wei ;
Chen, Xiao-Wei ;
Qi, Feng-Ming ;
Chen, Shi-Wu ;
Zhang, Fu-Min .
ORGANIC LETTERS, 2020, 22 (14) :5314-5319
[9]   Redox Economy in Organic Synthesis [J].
Burns, Noah Z. ;
Baran, Phil S. ;
Hoffmann, Reinhard W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867
[10]   Modular Chemical Synthesis of Streptogramin and Lankacidin Antibiotics [J].
Cai, Lingchao ;
Seiple, Ian B. ;
Li, Qi .
ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (08) :1891-1908