Bioinspired Asymmetric Synthesis of Hispidanin A

	Bioinspired Asymmetric Synthesis of Hispidanin A
	Gong, Jianxian 1; Li, Fuzhuo 1; Tu, Qian 1; Chen, Sijia 1; Zhu, Lei 2; Lan, Yu 2; Yang, Zhen 1,3,4,5
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2017-05-15
卷号	56 期号:21 页码:5844-5848
关键词	asymmetric synthesis biosynthesis Diels-Alder reaction hispidanin A natural products
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.
WOS标题词	Science & Technology ; Physical Sciences
类目[WOS]	Chemistry, Multidisciplinary
研究领域[WOS]	Chemistry
关键词[WOS]	DIELS-ALDER REACTIONS ; ENANTIOSPECIFIC SYNTHESIS ; BIOMIMETIC SYNTHESES ; CHEMICAL-REACTIVITY ; ISODON-HISPIDA ; DITERPENOIDS ; CHEMISTRY ; RHIZOMES ; DENSITY ; THERMOCHEMISTRY
收录类别	SCI
语种	英语
WOS记录号	WOS:000400755800034
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/151991]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
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
推荐引用方式 GB/T 7714	Gong, Jianxian,Li, Fuzhuo,Tu, Qian,et al. Bioinspired Asymmetric Synthesis of Hispidanin A[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56(21):5844-5848.
APA	Gong, Jianxian.,Li, Fuzhuo.,Tu, Qian.,Chen, Sijia.,Zhu, Lei.,...&Yang, Zhen.(2017).Bioinspired Asymmetric Synthesis of Hispidanin A.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,56(21),5844-5848.
MLA	Gong, Jianxian,et al."Bioinspired Asymmetric Synthesis of Hispidanin A".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.21(2017):5844-5848.