中国科学院机构知识库网格
Chinese Academy of Sciences Institutional Repositories Grid
首页 机构 成果 学者
  
  1. CAS IR Grid
  2. 上海药物研究所
  3. 中国科学院上海药物研究所
  4. 新药研究国家重点实验室
(-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis

文献类型：期刊论文

作者Yan, Bing-Chao1,2,5; Zhou, Min1,2; Li, Jian5; Li, Xiao-Nian1,2; He, Shi-Jun3,4; Zuo, Jian-Ping3,4; Sun, Han-Dong1,2; Li, Ang5; Puno, Pema-Tenzin1,2
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2021-03-30
页码10
ISSN号1433-7851
关键词bioactivity cyclobutane natural products scalable synthesis structure elucidation
DOI10.1002/anie.202100288
通讯作者Li, Ang(ali@sioc.ac.cn) ; Puno, Pema-Tenzin(punopematenzin@mail.kib.ac.cn)
英文摘要(-)-Isoscopariusin A was isolated from the aerial parts of Isodon scoparius. Chemical synthesis and spectroscopic analysis established its structure as an unsymmetrical meroditerpenoid bearing a sterically congested 6/6/4 tricyclic carbon skeleton with seven continuous stereocenters. A gram-scale synthesis was achieved in 12 steps from commercially available (+)-sclareolide. A cobalt catalyzed, hydrogen atom transfer-based olefin isomerization was used to prepare a trisubstituted alkene, which underwent stereoselective [2+2] cycloaddition with a substituted keteniminium ion generated in situ from the corresponding amide. The cyclobutanone product was further elaborated into the fully substituted cyclobutane core through face-selective homologation, and the two side chains were installed by using nickel-catalyzed cross-electrophile coupling and carbodiimide-mediated esterification, respectively. (-)-Isoscopariusin A displayed selective inhibition of T-cell proliferation.
资助项目Second Tibetan Plateau Scientific Expedition and Research (STEP) program[2019QZKK0502] ; NSFC-Joint Foundation of Yunnan Province[U2002221] ; National Natural Science Foundation of China[81673329] ; National Natural Science Foundation of China[21931014] ; National Natural Science Foundation of China[22007089] ; Chinese Academy of Sciences (Strategic Priority Research Program)[XDB20000000] ; Chinese Academy of Sciences (Key Research Program of Frontier Sciences)[QYZDB-SSW-SLH040] ; CAS Light of West China Program ; CAS Interdisciplinary Innovation ; Yunnan Science Fund for Distinguished Young Scholars[2019FJ002]
WOS研究方向Chemistry
语种英语
出版者WILEY-V C H VERLAG GMBH
WOS记录号WOS:000634847000001
源URL[http://119.78.100.183/handle/2S10ELR8/295459]  
专题新药研究国家重点实验室
通讯作者Li, Ang; Puno, Pema-Tenzin
作者单位1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, Lab Immunopharmacol, State Key Lab Drug Res, Shanghai 201203, Peoples R China
4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
5.Chinese Acad Sci, Univ Chinese Acad Sci, Ctr Excellence Mol Synth, State Key Lab Bioorgan & Nat Prod Chem,Shanghai I, 345 Lingling Rd, Shanghai 200032, Peoples R China
推荐引用方式
GB/T 7714		 Yan, Bing-Chao,Zhou, Min,Li, Jian,et al. (-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021:10.
APA Yan, Bing-Chao.,Zhou, Min.,Li, Jian.,Li, Xiao-Nian.,He, Shi-Jun.,...&Puno, Pema-Tenzin.(2021).(-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,10.
MLA Yan, Bing-Chao,et al."(-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021):10.

入库方式： OAI收割

来源：上海药物研究所

浏览0
下载0
收藏0
其他版本

除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。