Bioinspired Asymmetric Synthesis of Hispidanin A

doi:10.1002/anie.201700838

CORC > 北京大学 > 化学与分子工程学院

	Bioinspired Asymmetric Synthesis of Hispidanin A
	Li, Fuzhuo ; Tu, Qian ; Chen, Sijia ; Zhu, Lei ; Lan, Yu ; Gong, Jianxian ; Yang, Zhen
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2017
关键词	asymmetric synthesis biosynthesis Diels-Alder reaction hispidanin A natural products DIELS-ALDER REACTIONS ENANTIOSPECIFIC SYNTHESIS BIOMIMETIC SYNTHESES CHEMICAL-REACTIVITY ISODON-HISPIDA DITERPENOIDS CHEMISTRY RHIZOMES DENSITY THERMOCHEMISTRY
DOI	10.1002/anie.201700838
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.; National Science Foundation of China [21372016, 21572009, 21402002]; Guangdong Natural Science Foundation [2014A030312004, 2016A030306011]; Shenzhen Basic Research Program [ZDSYS20140509094114168, JSGG20140717102922014, JCYJ20150629144231017]; SCI(E); ARTICLE; 21; 5844-5848; 56
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/473412]
专题	化学与分子工程学院生命科学学院
推荐引用方式 GB/T 7714	Li, Fuzhuo,Tu, Qian,Chen, Sijia,et al. Bioinspired Asymmetric Synthesis of Hispidanin A[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017.
APA	Li, Fuzhuo.,Tu, Qian.,Chen, Sijia.,Zhu, Lei.,Lan, Yu.,...&Yang, Zhen.(2017).Bioinspired Asymmetric Synthesis of Hispidanin A.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA	Li, Fuzhuo,et al."Bioinspired Asymmetric Synthesis of Hispidanin A".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017).