Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine

doi:10.1021/jo1023188

	Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine
	Yang, Yu-Rong1 ; Shen, Liang 1,3; Huang, Jiu-Zhong 1,2; Xu, Tao 1,3; Wei, Kun 1
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
	2011-05-20
发表期刊	JOURNAL OF ORGANIC CHEMISTRY
ISSN	0022-3263
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
学科领域	Chemistry
DOI	10.1021/jo1023188
收录类别	SCI ; IC ; CCR
语种	英语
WOS记录号	WOS:000290465700009
引用统计
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
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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