Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine | |
Yang, Yu-Rong1; Shen, Liang1,3; Huang, Jiu-Zhong1,2; Xu, Tao1,3; Wei, Kun1 | |
刊名 | JOURNAL OF ORGANIC CHEMISTRY |
2011-05-20 | |
卷号 | 76期号:10页码:3684-3690 |
关键词 | SERRATININE (+)-FAWCETTIMINE |
ISSN号 | 0022-3263 |
通讯作者 | Yang, YR (reprint author), Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China |
英文摘要 | A unified strategy for total synthesis of the Lycopodium alkaloids (-)-8-deoxyserratinine (7), (+)-fawcettimine (1), and (+)-lycoflexine (4) is detailed. The key features include a highly efficient Helquist annulation to assemble the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, providing access to the common tricyclic skeleton, asymmetric Shi epoxidation, delivering the desired beta-epoxide stereospecifically to furnish (-)-8-deoxyserratinine (7), SmI(2) reduction of dihydroxylation derivative 35 to enable formation of (+)-fawcettimine (1), and a rapid biomimetic transformation of (+)-fawcettimine (1) into (+)-lycoflexine (4) via an intramolecular Mannich cyclization. |
学科主题 | Chemistry |
类目[WOS] | Chemistry, Organic |
研究领域[WOS] | Chemistry |
关键词[WOS] | SERRATININE ; (+)-FAWCETTIMINE |
收录类别 | SCI ; IC ; CCR |
资助信息 | National Natural Science of China[20802084, 21072200]; National Basic Research Program of China (973 Program)[2009CB522300]; Chinese Academy of Sciences; State Key Laboratory of Phytochemistry and Plant Resources in West China |
语种 | 英语 |
WOS记录号 | WOS:000290465700009 |
公开日期 | 2012-04-10 |
内容类型 | 期刊论文 |
源URL | [http://ir.kib.ac.cn/handle/151853/5451] |
专题 | 昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室 |
作者单位 | 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China 2.Yunnan Univ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China 3.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China |
推荐引用方式 GB/T 7714 | Yang, Yu-Rong,Shen, Liang,Huang, Jiu-Zhong,et al. Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(10):3684-3690. |
APA | Yang, Yu-Rong,Shen, Liang,Huang, Jiu-Zhong,Xu, Tao,&Wei, Kun.(2011).Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine.JOURNAL OF ORGANIC CHEMISTRY,76(10),3684-3690. |
MLA | Yang, Yu-Rong,et al."Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine".JOURNAL OF ORGANIC CHEMISTRY 76.10(2011):3684-3690. |
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