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
2011-05-20
发表期刊JOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
卷号76期号:10页码:3684-3690
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.
关键词Serratinine (+)-fawcettimine
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
学科领域Chemistry
DOI10.1021/jo1023188
收录类别SCI ; IC ; CCR
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000290465700009
引用统计
被引频次:39[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/5451
专题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
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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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