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题名: Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine
作者: null(杨玉荣)1; Shen, Liang1, 3; Huang, Jiu-Zhong1, 2; Xu, Tao1, 3; Wei, Kun1
刊名: JOURNAL OF ORGANIC CHEMISTRY
关键词: SERRATININE ; (+)-FAWCETTIMINE
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.
出版日期: 2011-05-20
卷号: 76, 期号:10, 页码:3684-3690
语种: 英语
收录类别: SCI ; IC ; CCR
学科分类: Chemistry
ISSN号: 0022-3263
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/5451
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Yang, YR; Shen, L; Huang, JZ; Xu, T; Wei, K.Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine,JOURNAL OF ORGANIC CHEMISTRY,2011,76(10):3684-3690
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