(-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis

doi:10.1002/anie.202100288

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	(-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis
	Yan,Bing-Chao ; Zhou,Min ; Li,Jian ; Li,Xiao-Nian ; He,Shi-Jun ; Zuo,Jian-Ping ; Sun,Han-Dong; Li,Ang ; Puno,Pema-Tenzin
	2021
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1433-7851
卷号	60 期号:23 页码:12859-12867
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.
关键词	bioactivity cyclobutane natural products scalable synthesis structure elucidation
DOI	10.1002/anie.202100288
WOS记录号	WOS:000634847000001
引用统计
文献类型	期刊论文
条目标识符	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.[Yan, Bing-Chao 2.Zhou, Min 3.Li, Xiao-Nian 4.Sun, Han-Dong 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 11.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,2021,60(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.

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