Total Synthesis of (-)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction

doi:10.1021/ol1012444

	Total Synthesis of (-)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction
	Yang, Yu-Rong1 ; Lai, Zeng-Wei 1,2; Shen, Liang 1; Huang, Jiu-Zhong 1,2; Wu, Xing-De 1; Yin, Jun-Lin 1; Wei, Kun 1
	2010-08-06
发表期刊	ORGANIC LETTERS
ISSN	1523-7060
卷号	12 期号:15 页码:3430-3433
摘要	The first enantioselective total synthesis of (-)-8-deoxyserratinine has been achieved in 15 steps from enone 4 with 7% overall yield. The key features include a highly efficient Helquist annulation to furnish the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, as well as asymmetric Shi epoxidation, delivering the desired beta-epoxide stereospecifically.
关键词	Lycopodium Alkaloids Absolute-configuration Lipogrammistin-a Serratinine 2-nitrobenzenesulfonamide Macrocyclization Serratum
学科领域	Chemistry, Organic
DOI	10.1021/ol1012444
收录类别	SCI ; IC ; CCR
语种	英语
WOS记录号	WOS:000280398900038
引用统计	被引频次：40[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/151853/4288
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, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China
推荐引用方式 GB/T 7714	Yang, Yu-Rong,Lai, Zeng-Wei,Shen, Liang,et al. Total Synthesis of (-)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction[J]. ORGANIC LETTERS,2010,12(15):3430-3433.
APA	Yang, Yu-Rong.,Lai, Zeng-Wei.,Shen, Liang.,Huang, Jiu-Zhong.,Wu, Xing-De.,...&Wei, Kun.(2010).Total Synthesis of (-)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction.ORGANIC LETTERS,12(15),3430-3433.
MLA	Yang, Yu-Rong,et al."Total Synthesis of (-)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction".ORGANIC LETTERS 12.15(2010):3430-3433.

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