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
Corresponding AuthorYang, YR (reprint author), Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China
2011-05-20
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume76Issue:10Pages:3684-3690
AbstractA 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.
KeywordSerratinine (+)-fawcettimine
Subject AreaChemistry
DOI10.1021/jo1023188
Indexed BySCI ; IC ; CCR
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000290465700009
Citation statistics
Cited Times:39[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/5451
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
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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