DICP OpenIR
Bioinspired Asymmetric Synthesis of Hispidanin A
Li, Fuzhuo1; Tu, Qian1; Chen, Sijia1; Zhu, Lei2; Lan, Yu2; Gong, Jianxian1; Yang, Zhen1,3,4,5
KeywordAsymmetric Synthesis Biosynthesis Diels-alder Reaction Hispidanin a Natural Products
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2017-05-15
DOI10.1002/anie.201700838
Volume56Issue:21Pages:5844-5848
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordDIELS-ALDER REACTIONS ; ENANTIOSPECIFIC SYNTHESIS ; BIOMIMETIC SYNTHESES ; CHEMICAL-REACTIVITY ; ISODON-HISPIDA ; DITERPENOIDS ; CHEMISTRY ; RHIZOMES ; DENSITY ; THERMOCHEMISTRY
AbstractThe first enantiospecific synthesis of hispidanin A (4), a dimeric diterpenoid from the rhizomes of Isodon hispida, was achieved with a longest linear sequence of 12 steps in 6.5% overall yield. A key component is the use of the abundant and naturally occurring diterpenoids (+)-sclareolide and (+)-sclareol as starting materials, which enables the gram-scale preparation of the key intermediates totarane (1) and s-trans-12E,14-labdadien-20,8 beta-olide (2). Subsequently a thermal or an erbium-catalyzed intermolecular Diels-Alder reaction of totarane (1) with labdadienolide (2) provide convergent and rapid access to the natural product hispidanin-A (4). The synthetic studies have offered significant impetus for the efficient construction of these architecturally complex natural products.
Language英语
WOS IDWOS:000400755800034
Citation statistics
Cited Times:10[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/151991
Collection中国科学院大连化学物理研究所
Affiliation1.Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China
2.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China
3.Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem & Mol Engn, Beijing 100871, Peoples R China
4.Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
5.Ocean Univ China, Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod Qingdao, 5 Yushan Rd, Qingdao 266003, Peoples R China
Recommended Citation
GB/T 7714
Li, Fuzhuo,Tu, Qian,Chen, Sijia,et al. Bioinspired Asymmetric Synthesis of Hispidanin A[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56(21):5844-5848.
APA Li, Fuzhuo.,Tu, Qian.,Chen, Sijia.,Zhu, Lei.,Lan, Yu.,...&Yang, Zhen.(2017).Bioinspired Asymmetric Synthesis of Hispidanin A.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,56(21),5844-5848.
MLA Li, Fuzhuo,et al."Bioinspired Asymmetric Synthesis of Hispidanin A".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.21(2017):5844-5848.
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