title: Total synthesis and stereochemical revision of xiamenmycin A.
abstract: The relative and absolute configurations of xiamenmycin A, a benzopyran compound isolated from Streptomyces xiamenensis 318 with a highly potent anti-fibrotic activity, have been characterized through the total synthesis. The key steps include the construction of the 3-chromanol moiety via Sharpless epoxidation followed by regio- and diastereo-selective cyclization and introduction of the threonine moiety at a later stage via Pd-catalysed aminocarbonylation in a one-pot procedure. The stereochemical assignment of natural xiamenmycin A has been accordingly revised to be 2R, 3S, 3'S, 4'R.
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Xiaozhen
authors.initials: X
authors.lastname: Jiao
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Yangyang
authors.initials: Y
authors.lastname: Yao
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Beibei
authors.initials: B
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Hongguang
authors.initials: H
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.affiliation: Institute of Oceanology and State Key Laboratory of Microbial Metabolism, Shanghai Jiao Tong University, Shanghai 200240, PR China.
authors.forename: Jun
authors.initials: J
authors.lastname: Xu
authors.affiliation: Key Laboratory of Systems Biomedicine, Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Shanghai 200240, PR China. minjuanxu@sjtu.edu.cn.
authors.forename: Minjuan
authors.initials: M
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, PR China. xp@imm.ac.cn.
authors.forename: Ping
authors.initials: P
authors.lastname: Xie
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013912:Threonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001578:Benzopyrans; C582113:N-((3,4-dihydro-3-hydroxy-2-methyl-2-(4'-methyl-3'-pentenyl)-2H-1-benzopyran-6-yl)carbonyl)threonine; D013912:Threonine