Copper-Mediated Dimerization to Access 3a,3a '-'Bispyrrolidinoindoline: Diastereoselective Synthesis of (+)-WIN 64821 and (-)-Ditryptophenaline
Liang, Kangjiang; Deng, Xu; Tong, Xiaogang; Li, Dashan; Ding, Ming; Zhou, Ankun; Xia, Chengfeng; Xia,CF (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Yunnan,Peoples R China.; xiachengfeng@mail.kib.ac.cn
2015-01-16
发表期刊ORGANIC LETTERS
卷号17期号:2页码:206-209
摘要A copper-mediated cyclization and dimerization of tryptamine or tryptophan was developed to generate a C-2-symmetry C-3(sp(3))C-3(sp(3)) bridge with two contiguous stereogenic quaternary carbons in one step. Impressively, the ratio between exo and endo cyclization products varies when different protecting groups of Nb are utilized. This dimerization reaction could be conducted in gram scale. With this dimerization method, both endocyclotryptophan (+)-WIN 64821 and exocyclotryptophan (-)-ditryptophenaline were synthesized in 5 steps.
资助信息National Natural Science Foundation of China [21272242, 21302193]; Yunnan High-End Technology Professionals Introduction Program [2010CI117]; National Basic Research Program of China [2011CB915503]
学科领域Chemistry, Organic
DOI10.1021/ol5032365
收录类别SCI ; IC ; CCR
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000348331800010
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文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/20589
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.; xiachengfeng@mail.kib.ac.cn
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GB/T 7714
Liang, Kangjiang,Deng, Xu,Tong, Xiaogang,et al. Copper-Mediated Dimerization to Access 3a,3a '-'Bispyrrolidinoindoline: Diastereoselective Synthesis of (+)-WIN 64821 and (-)-Ditryptophenaline[J]. ORGANIC LETTERS,2015,17(2):206-209.
APA Liang, Kangjiang.,Deng, Xu.,Tong, Xiaogang.,Li, Dashan.,Ding, Ming.,...&xiachengfeng@mail.kib.ac.cn.(2015).Copper-Mediated Dimerization to Access 3a,3a '-'Bispyrrolidinoindoline: Diastereoselective Synthesis of (+)-WIN 64821 and (-)-Ditryptophenaline.ORGANIC LETTERS,17(2),206-209.
MLA Liang, Kangjiang,et al."Copper-Mediated Dimerization to Access 3a,3a '-'Bispyrrolidinoindoline: Diastereoselective Synthesis of (+)-WIN 64821 and (-)-Ditryptophenaline".ORGANIC LETTERS 17.2(2015):206-209.
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