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Enantioselective Total Synthesis of (+)-Jungermatrobrunin A

文献类型：期刊论文

作者Wu, Jinbao1,2,3; Kadonaga, Yuichiro2,3; Hong, Benke2,3; Wang, Jin2,3; Lei, Xiaoguang2,3
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2019-08-05
卷号58期号:32页码:10879-10883
关键词peroxide formation photochemistry radical cyclization rearrangement total synthesis
ISSN号1433-7851
DOI10.1002/anie.201903682
通讯作者Lei, Xiaoguang(xglei@pku.edu.cn)
英文摘要A concise and enantioselective total synthesis of (+)-jungermatrobrunin A (1), which features a unique bicyclo[3.2.1]octene ring skeleton with an unprecedented peroxide bridge, was accomplished in 13 steps by making use of a late-stage visible-light-mediated Schenck ene reaction of (-)-1 alpha,6 alpha-diacetoxyjungermannenone C (2). Along the way, a UV-light-induced bicyclo[3.2.1]octene ring rearrangement afforded (+)-12-hydroxy-1 alpha,6 alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one (4). These divergent photo-induced skeletal rearrangements support a possible biogenetic relationship between (+)-1, (-)-2, and (+)-4.
WOS关键词ENT-KAURANE DITERPENOIDS ; 1ST TOTAL-SYNTHESIS ; LUNGSHENGENIN-D ; REARRANGEMENTS ; CONSTRUCTION ; CONVERSION ; KETONES ; ACID ; BETA
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000478635100014
出版者WILEY-V C H VERLAG GMBH
源URL[http://cas-ir.dicp.ac.cn/handle/321008/173424]  
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Lei, Xiaoguang
作者单位1.Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
2.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci, Minist Educ,Dept Chem Biol,Coll Chem & Mol Engn,S, Beijing 100871, Peoples R China
3.Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
推荐引用方式
GB/T 7714		 Wu, Jinbao,Kadonaga, Yuichiro,Hong, Benke,et al. Enantioselective Total Synthesis of (+)-Jungermatrobrunin A[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(32):10879-10883.
APA Wu, Jinbao,Kadonaga, Yuichiro,Hong, Benke,Wang, Jin,&Lei, Xiaoguang.(2019).Enantioselective Total Synthesis of (+)-Jungermatrobrunin A.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(32),10879-10883.
MLA Wu, Jinbao,et al."Enantioselective Total Synthesis of (+)-Jungermatrobrunin A".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.32(2019):10879-10883.

入库方式： OAI收割

来源：大连化学物理研究所

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