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题名: Bioinspired Asymmetric Synthesis of Hispidanin A
作者: Li, Fuzhuo1;  Tu, Qian1;  Chen, Sijia1;  Zhu, Lei2;  Lan, Yu2;  Gong, Jianxian1;  Yang, Zhen1, 3, 4, 5
关键词: asymmetric synthesis ;  biosynthesis ;  Diels-Alder reaction ;  hispidanin A ;  natural products
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
发表日期: 2017-05-15
DOI: 10.1002/anie.201700838
卷: 56, 期:21, 页:5844-5848
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: The 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.
关键词[WOS]: DIELS-ALDER REACTIONS ;  ENANTIOSPECIFIC SYNTHESIS ;  BIOMIMETIC SYNTHESES ;  CHEMICAL-REACTIVITY ;  ISODON-HISPIDA ;  DITERPENOIDS ;  CHEMISTRY ;  RHIZOMES ;  DENSITY ;  THERMOCHEMISTRY
语种: 英语
WOS记录号: WOS:000400755800034
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/151991
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.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:
Li, Fuzhuo,Tu, Qian,Chen, Sijia,et al. Bioinspired Asymmetric Synthesis of Hispidanin A[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56(21):5844-5848.
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