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Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B
Han, Jianguang1; Li, Xia1; Guan, Yong2; Zhao, Wenjun2; Wulff, William D.2; Lei, Xiaoguang3,4
KeywordBoron Cyclization Natural Products Synthetic Methods Total Synthesis
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2014-08-25
ISSN1433-7851
DOI10.1002/anie.201404499
Volume53Issue:35Pages:9257-9261
Indexed BySCI ; IC
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordCULTIVATED MULBERRY TREE ; MORUS-ALBA L ; VISIBLE-LIGHT PHOTOCATALYSIS ; DIELS-ALDER REACTIONS ; NANOPARTICLE CATALYSIS ; MORACEOUS PLANTS ; ROOT BARK ; BIOSYNTHESIS ; CONSTITUENTS ; ADDUCT
AbstractThe first enantioselective total syntheses of prenylflavonoid Diels Alder natural products (-)-kuwanon (-)-kuwanon J, (-)-brosimone A, and (-)-brosimone B have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels Alder cyclo-addition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem interlintramolecular asymmetric Diels Alder cycloaddition process was applied for the synthesis of (-)-brosimone A.
Language英语
WOS IDWOS:000342676100023
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Cited Times:21[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/167323
Collection中国科学院大连化学物理研究所
Corresponding AuthorWulff, William D.
Affiliation1.Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
2.Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
3.Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Dept Chem Biol,Coll Chem & Mol Engn,S, Beijing 100871, Peoples R China
4.Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Han, Jianguang,Li, Xia,Guan, Yong,et al. Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2014,53(35):9257-9261.
APA Han, Jianguang,Li, Xia,Guan, Yong,Zhao, Wenjun,Wulff, William D.,&Lei, Xiaoguang.(2014).Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,53(35),9257-9261.
MLA Han, Jianguang,et al."Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53.35(2014):9257-9261.
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