Photooxygenation of Furylalkylamines: Easy Access to Pyrrolizidine and Indolizidine Scaffolds.

作者: Dimitris Kalaitzakis , Myron Triantafyllakis , Manolis Sofiadis , Dimitris Noutsias , Georgios Vassilikogiannakis

DOI: 10.1002/ANIE.201600988

关键词: PyrrolizidineSequence (biology)Cascade reactionIndolizidineChemistryPhotooxygenationOrganic chemistry

摘要: A highly adaptable method targeting the ubiquitous and very important pyrrolizidine indolizidine scaffolds is presented. The general synthetic utility of underscored by its application to rapid easy synthesis five natural products starting from readily accessible alkylfuran precursors. These unprotected primary furylalkylamines are subjected photooxygenation conditions, which initiate a complex cascade reaction sequence concluding with production high value motifs. This can be tailored need varying choice both photosensitizer base additive.

参考文章(45)
David S. Seigler, Pyrrolizidine, Quinolizidine, and Indolizidine Alkaloids Springer, Boston, MA. pp. 546- 567 ,(1998) , 10.1007/978-1-4615-4913-0_30
Igor V. Trushkov, Maxim G. Uchuskin, Alexander V. Butin, Furan's Gambit: Electrophile‐Attack‐Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles European Journal of Organic Chemistry. ,vol. 2015, pp. 2999- 3016 ,(2015) , 10.1002/EJOC.201403580
YoungKu Kang, Matthew T Richers, Conrad H Sawicki, Daniel Seidel, None, C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds. Chemical Communications. ,vol. 51, pp. 10648- 10651 ,(2015) , 10.1039/C5CC03390J
Guillaume Lapointe, Kurt Schenk, Philippe Renaud, Concise Synthesis of Pyrrolidine and Indolizidine Alkaloids by a Highly Convergent Three‐Component Reaction Chemistry: A European Journal. ,vol. 17, pp. 3207- 3212 ,(2011) , 10.1002/CHEM.201003137
John W. Daly, Thomas F. Spande, H. Martin Garraffo, Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds. Journal of Natural Products. ,vol. 68, pp. 1556- 1575 ,(2005) , 10.1021/NP0580560
S.H. Goh, Chen Wei, Abdul Razak Mohd. Ali, Strychnos - Aspidosperma alkaloids and a novel hydroxydilactam artefact from (Apocynaceae) Tetrahedron Letters. ,vol. 25, pp. 3483- 3484 ,(1984) , 10.1016/S0040-4039(01)91054-8
Falko Abels, Chris Lindemann, Eva Koch, Christoph Schneider, A general organocatalytic approach toward the enantioselective total synthesis of indolizidine based alkaloids. Organic Letters. ,vol. 14, pp. 5972- 5975 ,(2012) , 10.1021/OL302871U
H. M. Garraffo, J. Caceres, J. W. Daly, T. F. Spande, N. R. Andriamaharavo, M. Andriantsiferana, Alkaloids in Madagascan frogs (Mantella): pumiliotoxins, indolizidines, quinolizidines, and pyrrolizidines. Journal of Natural Products. ,vol. 56, pp. 1016- 1038 ,(1993) , 10.1021/NP50097A005