Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization
Deng, Xu1; Liang, Kangjiang1,2; Tong, Xiaogang1,2; Ding, Ming1,2; Li, Dashan1,2; Xia, Chengfeng1; Xia,CF (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Yunnan,Peoples R China.; xia-chengfeng@mail.kib.ac.cn
2015-06-03
发表期刊TETRAHEDRON
卷号71期号:22页码:3699-3704
摘要Synthetic endeavors toward (-)-chaetominine via copper-catalyzed radical cyclization are reported. Both of the pyrido[2,3,b]-indole ring (C ring) and imidazolidinone (D ring) are efficiently constructed in one-pot manner. It's unveiled that the newly formed stereo center is controlled by the chiral of alanine, not by tryptophan. With these synthetic discoveries, highly efficient and diastereoselective synthesis of (+)-2,3,14-epi-chaetominine 5 and (-)-11-epi-chaetominine 11 is achieved. (C) 2014 Elsevier Ltd. All rights reserved.
关键词Indole Alkaloids (-)-chaetominine Total Synthesis Copper-catalyzed Cyclization
资助信息National Natural Science Foundation of China [21272242, 21302193]; Yunnan High-End Technology Professionals Introduction Program [2010CI117]; West Doctor Foundation of Chinese Academy of Sciences [292014312D11016]; National Basic Research Program of China [2011CB915500]
收录类别SCI
语种英语
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文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/21344
专题植物化学与西部植物资源持续利用国家重点实验室
通讯作者Xia,CF (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Yunnan,Peoples R China.; xia-chengfeng@mail.kib.ac.cn
作者单位1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
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Deng, Xu,Liang, Kangjiang,Tong, Xiaogang,et al. Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization[J]. TETRAHEDRON,2015,71(22):3699-3704.
APA Deng, Xu.,Liang, Kangjiang.,Tong, Xiaogang.,Ding, Ming.,Li, Dashan.,...&xia-chengfeng@mail.kib.ac.cn.(2015).Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization.TETRAHEDRON,71(22),3699-3704.
MLA Deng, Xu,et al."Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization".TETRAHEDRON 71.22(2015):3699-3704.
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