| 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
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| 2015-01-16 | |
| Source Publication | ORGANIC LETTERS
 |
| Volume | 17Issue:2Pages:206-209 |
| Abstract | 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. |
| Subject Area | Chemistry, Organic |
| DOI | 10.1021/ol5032365 |
| Indexed By | SCI ; IC ; CCR |
| Language | 英语 |
| WOS Research Area | Chemistry |
| WOS Subject | Chemistry, Organic |
| WOS ID | WOS:000348331800010 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://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 Author | 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 |
| 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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| File Name/Size | DocType | Version | Access | License | ||
| ol5032365.pdf（629KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Download | |
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