Total Synthesis of (-)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction
Yang, Yu-Rong1; Lai, Zeng-Wei1,2; Shen, Liang1; Huang, Jiu-Zhong1,2; Wu, Xing-De1; Yin, Jun-Lin1; Wei, Kun1
2010-08-06
发表期刊ORGANIC LETTERS
ISSN1523-7060
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
资助信息National Natural Science of China [20802084]; National Basic Research Program of China (973 Program) [2009 CB522300]; Chinese Academy of Sciences ; State Key Laboratory of Phytochemistry and Plant Resources in West China
收录类别SCI ; IC ; CCR
语种英语
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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
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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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