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
Source PublicationORGANIC LETTERS
Volume17Issue:2Pages:206-209
AbstractA 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.
Subject AreaChemistry, Organic
DOI10.1021/ol5032365
Indexed BySCI ; IC ; CCR
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000348331800010
Citation statistics
Cited Times:22[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/20589
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorXia,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
Recommended Citation
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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