Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation
Dong, Liao-Bin1,2; Wu, Ya-Nan1,2; Jiang, Shi-Zhi1,2; Wu, Xing-De1; He, Juan1; Yang, Yu-Rong1; Zhao, Qin-Shi1
2014-05-16
发表期刊ORGANIC LETTERS
ISSN1523-7060
卷号16期号:10页码:2700-2703
摘要Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C17N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymmetric total synthesis. Following the first total synthesis of lobscurinine (3), 1 was achieved via regio- and stereoselective cyanide ion addition and subsequent acid treatment.
关键词Fawcettimine-related Alkaloids Alpha Unified Total Syntheses Beta-unsaturated Carbonyl-compounds Palhinhaea-cernua Unprecedented Skeleton Helquist Annulation A-c Japonicum (-)-8-deoxyserratinine (+)-lycoflexine
资助信息National Natural Science Foundation [U0932602, 90813004, 2009312311024, 21072200]; 973 Program [2009CB522300, 2011CB915503]
学科领域Chemistry
DOI10.1021/ol500978k
收录类别SCI ; IC
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000336199200033
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被引频次:18[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/151853/18102
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 West Ch, Kunming 650201, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100039, Peoples R China
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Dong, Liao-Bin,Wu, Ya-Nan,Jiang, Shi-Zhi,et al. Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation[J]. ORGANIC LETTERS,2014,16(10):2700-2703.
APA Dong, Liao-Bin.,Wu, Ya-Nan.,Jiang, Shi-Zhi.,Wu, Xing-De.,He, Juan.,...&Zhao, Qin-Shi.(2014).Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation.ORGANIC LETTERS,16(10),2700-2703.
MLA Dong, Liao-Bin,et al."Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation".ORGANIC LETTERS 16.10(2014):2700-2703.
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