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Divergent Total Synthesis of the Lycopodium Alkaloids Huperzine A, Huperzine B, and Huperzine U
Alternative Title石松类生物碱石杉碱甲、石杉碱乙和石杉碱U的发散式全合成
Ding R(丁瑞); Fu JG(付建国); Xu GQ(徐广强); Sun BF(孙炳峰); Lin GQ(林国强)
2014
Source PublicationJ. Org. Chem.
Volume79Issue:1Pages:240-250
AbstractHuperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (=Lycopodium serratum) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total. syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.
Subject Area天然产物有机化学
DOI10.1021/jo402419h
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Indexed BySCI
Language英语
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38967
Collection中科院天然产物有机化学重点实验室
Corresponding AuthorSun BF(孙炳峰); Lin GQ(林国强)
Affiliation中国科学院上海有机化学研究所, 天然产物有机合成化学重点实验室
Recommended Citation
GB/T 7714
Ding R,Fu JG,Xu GQ,et al. Divergent Total Synthesis of the Lycopodium Alkaloids Huperzine A, Huperzine B, and Huperzine U[J]. J. Org. Chem.,2014,79(1):240-250.
APA 丁瑞,付建国,徐广强,孙炳峰,&林国强.(2014).Divergent Total Synthesis of the Lycopodium Alkaloids Huperzine A, Huperzine B, and Huperzine U.J. Org. Chem.,79(1),240-250.
MLA 丁瑞,et al."Divergent Total Synthesis of the Lycopodium Alkaloids Huperzine A, Huperzine B, and Huperzine U".J. Org. Chem. 79.1(2014):240-250.
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