title: Scopariusicides, Novel Unsymmetrical Cyclobutanes: Structural Elucidation and Concise Synthesis by a Combination of Intermolecular [2 + 2] Cycloaddition and C-H Functionalization.
abstract: Scopariusicides A (1) and B (2), two novel immunosuppressive unsymmetrical cyclobutane derivatives, were isolated from the aerial parts of Isodon scoparius. Moreover, based on the results of phytochemical investigation, a concise stereocontrolled synthesis of scopariusicide A and its analogues with enhanced biological activities was efficiently achieved using the main diterpenoid (3) isolated from this plant as a readily available starting material. A crossed intermolecular [2 + 2] photocycloaddition and a Pd-catalyzed sp(3) C-H bond β-arylation were used synergistically to access the highly congested unsymmetrical cyclobutane core with four contiguous stereocenters.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.|Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University , Kunming 650031, P. R. China.
authors.forename: Min
authors.initials: M
authors.lastname: Zhou
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.|University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
authors.forename: Xing-Ren
authors.initials: XR
authors.lastname: Li
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.|University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
authors.forename: Jian-Wei
authors.initials: JW
authors.lastname: Tang
authors.affiliation: Department of Immunology, School of Basic Medical Sciences, Chengdu Medical College , Chengdu 610083, P. R. China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Xiao-Nian
authors.initials: XN
authors.lastname: Li
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Bin
authors.initials: B
authors.lastname: Wu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Hong-Bo
authors.initials: HB
authors.lastname: Qin
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Xue
authors.initials: X
authors.lastname: Du
authors.affiliation: Department of Immunology, School of Basic Medical Sciences, Chengdu Medical College , Chengdu 610083, P. R. China.
authors.forename: Li-Mei
authors.initials: LM
authors.lastname: Li
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Wei-Guang
authors.initials: WG
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Jian-Xin
authors.initials: JX
authors.lastname: Pu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, P. R. China.
authors.forename: Han-Dong
authors.initials: HD
authors.lastname: Sun
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D055808:Drug Discovery; D006801:Humans; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D037602:Isodon / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013601:T-Lymphocytes / Q000187:drug effects
chemical_list: D003503:Cyclobutanes; D007166:Immunosuppressive Agents; C000606890:scopariusicide A; C000606892:scopariusicide B