(-)-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-Chao; Zhou,Min; Li,Jian; Li,Xiao-Nian; He,Shi-Jun; Zuo,Jian-Ping; Sun,Han-Dong ; Li,Ang; Puno,Pema-Tenzin
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| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2021 |
| 卷号 | 60期号:23页码:12859-12867 |
| ISSN号 | 1433-7851 |
| 关键词 | bioactivity cyclobutane natural products scalable synthesis structure elucidation |
| DOI | 10.1002/anie.202100288 |
| 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. |
| WOS记录号 | WOS:000634847000001 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/73365]  |
| 专题 | 中国科学院昆明植物研究所 |
| 作者单位 | 1.Li, Xiao-Nian 2.Sun, Han-Dong 3.[Yan, Bing-Chao 4.Zhou, Min 5.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 6.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China 7.[He, Shi-Jun 8.Chinese Acad Sci, Shanghai Inst Mat Med, Lab Immunopharmacol, State Key Lab Drug Res, Shanghai 201203, Peoples R China 9.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 10.Li, Jian |
| 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,2021,60(23):12859-12867. |
| 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,60(23),12859-12867. |
| MLA | Yan,Bing-Chao,et al."(-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60.23(2021):12859-12867. |
入库方式： OAI收割
来源：昆明植物研究所
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