Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition
文献类型：期刊论文
| 作者 | Yang, Zhen1,3,4,5,6; Long, Rong1,4,5,6; Huang, Jun1,4,5,6; Shao, Wenbin1,4,5,6; Liu, Song2; Lan, Yu2; Gong, Jianxian1,4,5,6 |
| 刊名 | NATURE COMMUNICATIONS
 |
| 出版日期 | 2014-12-01 |
| 卷号 | 5 |
| ISSN号 | 2041-1723 |
| DOI | 10.1038/ncomms6707 |
| 文献子类 | Article |
| 英文摘要 | The development of efficient reactions for the one-pot construction of bicyclic ring systems bearing two quaternary carbon centres at their bridgehead positions represents a significant challenge to synthetic chemistry. The development of new methods capable of overcoming this challenge is highly desirable, because this motif can be found in a wide range of natural products with significant biological activities. Herein, we report an efficient [3+2] cycloaddition reaction between an enal and an alleno rhodium species, which was generated in situ from the corresponding enynol via a retro metal-propargylation reaction, to give [3.3.0] and [3.4.0] bicyclic systems bearing two quaternary atoms at their bridgehead positions. The developed chemistry has been successfully applied to the asymmetric total synthesis of natural product (-)-lingzhiol (4) for the first time in 17 steps. |
| WOS关键词 | CARBON QUATERNARY STEREOCENTERS ; ELECTRON-DEFICIENT OLEFINS ; DOUBLE MICHAEL ADDITION ; ENANTIOSELECTIVE CONSTRUCTION ; FUNCTIONALIZED CYCLOPENTENES ; CYCLOTRYPTAMINE ALKALOIDS ; CONJUGATE ADDITION ; PALLADIUM ; ACID ; ALLENES |
| WOS研究方向 | Science & Technology - Other Topics |
| 语种 | 英语 |
| WOS记录号 | WOS:000347229300003 |
| 出版者 | NATURE PUBLISHING GROUP |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/167352]  |
| 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 | Lan, Yu |
| 作者单位 | 1.Peking Univ, Acad Adv Interdisciplinary Studies, Beijing 100871, Peoples R China 2.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China 3.Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Chinese Minist Educ, Qingdao 266003, Peoples R China 4.Peking Univ, Shenzhen Grad Sch, Lab Chem Genom, Sch Chem Biol & Biotechnol, Shenzhen 518055, Peoples R China 5.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China 6.Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China |
| 推荐引用方式 GB/T 7714 | Yang, Zhen,Long, Rong,Huang, Jun,et al. Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition[J]. NATURE COMMUNICATIONS,2014,5. |
| APA | Yang, Zhen.,Long, Rong.,Huang, Jun.,Shao, Wenbin.,Liu, Song.,...&Gong, Jianxian.(2014).Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition.NATURE COMMUNICATIONS,5. |
| MLA | Yang, Zhen,et al."Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition".NATURE COMMUNICATIONS 5(2014). |
入库方式： OAI收割
来源：大连化学物理研究所
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