Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B

doi:10.1002/anie.201404499

	Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B
	Han, Jianguang 3; Li, Xia 3; Guan, Yong 4; Zhao, Wenjun 4; Wulff, William D.4; Lei, Xiaoguang 1,2
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2014-08-25
卷号	53 期号:35 页码:9257-9261
关键词	Boron Cyclization Natural Products Synthetic Methods Total Synthesis
ISSN号	1433-7851
DOI	10.1002/anie.201404499
文献子类	Article
英文摘要	The 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.
WOS关键词	CULTIVATED MULBERRY TREE ; MORUS-ALBA L ; VISIBLE-LIGHT PHOTOCATALYSIS ; DIELS-ALDER REACTIONS ; NANOPARTICLE CATALYSIS ; MORACEOUS PLANTS ; ROOT BARK ; BIOSYNTHESIS ; CONSTITUENTS ; ADDUCT
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000342676100023
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/167322]
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
通讯作者	Wulff, William D.
作者单位	1.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 2.Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China 3.Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China 4.Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
推荐引用方式 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.