CAS: 20316-18-1; Lycodine

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    (4Ar,5S,10Br,12R)-1-Benzyl-12-Methyl-2,3,4,4A,5,6-Hexahydro-1H-5,10B-Propano-1,7-Phenanthroline 1438285-59-6
    Boc-Lycodine 1225450-38-3
    (4Ar,5S,10Br,12R)-1-Benzyl-12-Methyl-9-(Trimethylsilyl)-2,3,4,4A,5,6-Hexahydro-1H-5,10B-Propano-1,7-Phenanthroline 1438285-58-5
    Benzyl (1R,9S,10R,16S)-16-Methyl-17-Oxo-6,14-Diazatetracyclo[7.5.3.01,10.02,7]Heptadeca-2(7),3,5-Triene-14-Carboxylate 1448802-15-0

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      📜长叶薄荷酮置于咪唑,正丁基锂,Magnesium(II) Perchlorate,Carbon Monoxide,Cobalt,Cyclopenta-1,3-Diene,Palladium 10% On Activated Carbon,四丁基氟化铵,水,氢气,Sodium Hydride,Potassium Carbonate,间氯过氧苯甲酸,三苯基膦,Copper(L) Chloride,Lithium Hydroxide体系中,用 四氢呋喃,甲醇,四氯化碳,乙醚,正己烷,二氯甲烷,N,N-二甲基甲酰胺,氯苯,甲苯,Mineral Oil 用作溶剂,化学反应 140.89H,反应生成(4Ar,12R)-2,3,4,4Abeta,5,6-六氢-12-甲基-1H-5Beta,10Bbeta-丙桥-1,7-菲咯啉
      参考文献:Syntheses Of (+)-Complanadine A And Lycodine Derivatives By Regioselective [2 + 2 + 2] Cycloadditions
      标题:Syntheses Of (+)-Complanadine A And Lycodine Derivatives By Regioselective [2 + 2 + 2] Cycloadditions
      摘要:The Dimeric Alkaloid Complanadine A Has Shown Promise In Regenerative Science,Promoting Neuronal Growth By Inducing The Secretion Of Growth Factors From Glial Cells. Through The Use Of Tandem,Cobalt-Mediated [2 + 2 + 2] Cycloaddition Reactions,Two Synthetic Routes Have Been Developed With Different Sequences For The Formation Of The Unsymmetric Bipyridyl Core. The Regioselective Formation Of Each Of The Pyridines Was Achieved Based On The Inherent Selectivity Of The Molecules Or By Reversing The Regioselectivity Through The Addition Of Lewis Bases. This Strategy Has Been Successfully Employed To Provide Laboratory Access To Complanadine A As Well As Structurally Related Compounds Possessing The Lycocline Core.
      Doi:10.1021/jo400695C

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      主要参考文献


      1: Qu SM, Shan BH, Wang HT, Wang S. Lycodine type alkaloids from Lycopodiastrum casuarinoides with cytotoxic and cholinesterase inhibitory activities. Fitoterapia. 2018 Nov;131:86-90. doi: 10.1016/j.fitote.2018.10.021. Epub 2018 Oct 21. doi: 10.1016/j.fitote.2018.09.005. Epub 2018 Sep 11. doi: 10.1016/j.phytochem.2018.06.016. Epub 2018 Jul 5. doi: 10.1007/s13659-017-0140-z. Epub 2017 Jul 25.
      5: Tang Y, Xiong J, Zou Y, Wang W, Huang C, Zhang HY, Hu JF. Annotinolide F and lycoannotines A-I, further Lycopodium alkaloids from Lycopodium annotinum. Phytochemistry. 2017 Nov;143:1-11. doi: 10.1016/j.phytochem.2017.07.003. Epub 2017 Jul 21. doi: 10.1016/j.fitote.2016.10.005. Epub 2016 Oct 18. doi: 10.1002/chem.201604647. Epub 2016 Nov 25. J Ethnopharmacol. 2016 Dec 4;193:546-554. doi: 10.1016/j.jep.2016.09.049. Epub 2016 Sep 28. doi: 10.1002/bmc.3723. Epub 2016 Apr 27. doi: 10.1186/s12906-015-0867-1.
      11: Shaikh S, Zainab T, Shakil S, Rizvi SM. A neuroinformatics study to compare inhibition efficiency of three natural ligands (Fawcettimine, Cernuine and Lycodine) against human brain acetylcholinesterase. Network. 2015;26(1):25-34. doi: 10.3109/0954898X.2014.994145. Epub 2015 Jan 22. doi: 10.1080/14786419.2014.984184. Epub 2014 Nov 25. doi: 10.1002/rcm.7061. doi: 10.1016/j.fitote.2014.09.005. Epub 2014 Sep 16. doi: 10.1021/ja507016g. Epub 2014 Aug 11. doi: 10.3390/molecules19079999. doi: 10.1016/j.bmcl.2014.05.060. Epub 2014 May 27. doi: 10.1016/S1875-5364(14)60046-7. doi: 10.1021/np4003355. Epub 2013 Aug 13. doi: 10.1021/jo401014n. Epub 2013 Jun 10.

      合成参考文献


      参考文献:10.1016/s0031-9422(00)86930-7
      摘要:Braekman JC, Nyembo L, Bourdoux P, Kahindo N, Hootele C. Distribution des alcaloides dans le genre Lycopodium. Phytochemistry. 1974 Nov;13(11):2519–28. doi: 10.1016/s0031-9422(00)86930-7.
      参考文献:10.1016/0031-9422(79)80193-4
      摘要:Loyola LA, Morales G, Castillo M. Alkaloids of Lycopodium magellanicum. Phytochemistry. 1979 Sep;18(10):1721–3. doi: 10.1016/0031-9422(79)80193-4.
      参考文献:10.1055/s-0034-1378706
      摘要:Masson G, Courant T, Dagousset G. Enamide Derivatives: Versatile Building Blocks for Total Synthesis. Synthesis. 2015 May 27;47(13):1799–856. doi: 10.1055/s-0034-1378706.
      参考文献:10.1055/s-0036-1591979
      摘要:Larson G. Some Aspects of the Chemistry of Alkynylsilanes. Synthesis. 2018 May 18;50(13):2433–62. doi: 10.1055/s-0036-1591979.
      参考文献:10.1139/v03-067
      摘要:Tan C, Ma X, Chen G, Zhu D. Huperzines S, T, and U: New Lycopodium alkaloids from Huperzia serrata. Can. J. Chem. 2003 Apr 01;81(4):315–8. doi: 10.1139/v03-067.
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