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Pure Appl. Chem., 2010, Vol. 82, No. 11, pp. 1975-1991

http://dx.doi.org/10.1351/PAC-CON-09-12-15

Published online 2010-08-06

Total synthesis of biologically active alkaloids using transition metals

Ronny Forke1, Konstanze K. Gruner1, Kerstin E. Knott1, Stefan Auschill1, Sameer Agarwal1, René Martin1, Markus Böhl2, Sabine Richter2, Georgios Tsiavaliaris3, Roman Fedorov3, Dietmar J. Manstein3, Herwig O. Gutzeit2 and Hans-Joachim Knölker1*

1 Department of Chemistry, Technical University of Dresden, Bergstrasse 66, 01069 Dresden, Germany
2 Institute of Zoology, Technical University of Dresden, Zellescher Weg 20b, 01217 Dresden, Germany
3 Institute for Biophysical Chemistry, Hannover Medical School, 30623 Hannover, Germany

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  • Kumar V. Pavan, Gruner Konstanze K., Kataeva Olga, Knölker Hans-Joachim: Total Synthesis of the Biscarbazole Alkaloids Murrafoline A-D by a Domino Sonogashira Coupling/Claisen Rearrangement/Electrocyclization Reaction. Angew. Chem. 2013, 125, 11279. <http://dx.doi.org/10.1002/ange.201305993>
  • Kumar V. Pavan, Gruner Konstanze K., Kataeva Olga, Knölker Hans-Joachim: Total Synthesis of the Biscarbazole Alkaloids Murrafoline A-D by a Domino Sonogashira Coupling/Claisen Rearrangement/Electrocyclization Reaction. Angew. Chem. Int. Ed. 2013, 52, 11073. <http://dx.doi.org/10.1002/anie.201305993>
  • Hieda Yuhzo, Choshi Tominari, Fujioka Haruto, Hibino Satoshi: Total Synthesis of the Neuronal Cell-Protecting Carbazole Alkaloids Carbazomadurin A and (S )-(+)-Carbazomadurin B. Eur. J. Org. Chem. 2013, 2013, 7391. <http://dx.doi.org/10.1002/ejoc.201301059>
  • Reddy B.V. Subba, Reddy P. Sivaramakrishna, Yadav J.S., Sridhar B.: Novel protocol for the synthesis of octahydropyrano- and thiopyrano[4,3-a]carbazole derivatives via Prins/Friedel–Crafts cyclization. Tetrahedron Letters 2013, 54, 1392. <http://dx.doi.org/10.1016/j.tetlet.2012.12.113>
  • Agarwal Sameer, Kataeva Olga, Schmidt Ulrike, Knölker Hans-Joachim: Silver(i)-promoted oxidative cyclisation to pyrrolo[2,1-a]isoquinolines and application to the synthesis of (±)-crispine A. RSC Adv. 2013, 3, 1089. <http://dx.doi.org/10.1039/c2ra22823h>
  • Gensch Tobias, Rönnefahrt Marika, Czerwonka Regina, Jäger Anne, Kataeva Olga, Bauer Ingmar, Knölker Hans-Joachim: Snapshot of the Palladium(II)-Catalyzed Oxidative Biaryl Bond Formation by X-ray Analysis of the Intermediate Diaryl Palladium(II) Complex. Chemistry A European Journal 2012, 18, 770. <http://dx.doi.org/10.1002/chem.201103576>
  • Kumar Chepuri V. Suneel, Puranik Vedavati G, Ramana Chepuri V.: InCl3-Mediated Addition of Indole to Isatogens: An Expeditious Synthesis of 13-deoxy-Isatisine A. Chem. Eur. J. 2012, 18, 9601. <http://dx.doi.org/10.1002/chem.201103604>
  • Ali Khan Monika, Mahon Mary F., Lowe John P., Stewart Alan J. W., Lewis Simon E.: Valuable New Cyclohexadiene Building Blocks from Cationic η5 -Iron-Carbonyl Complexes Derived from a Microbial Arene Oxidation Product. Chem. Eur. J. 2012, 18, 13480. <http://dx.doi.org/10.1002/chem.201202411>
  • Lennartz Petra, Raabe Gerhard, Bolm Carsten: Synthesis of Planar Chiral Carbazole Derivatives Bearing a [2.2]Paracyclophane Skeleton. Isr J Chem 2012, 52, 171. <http://dx.doi.org/10.1002/ijch.201100070>
  • Schmidt Arndt W., Reddy Kethiri R., Knölker Hans-Joachim: Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids. Chem. Rev. 2012, 112, 3193. <http://dx.doi.org/10.1021/cr200447s>
  • Stephenson G. Richard, Roe Caroline, Anson Christopher E.: Stereochemical Requirements of Oxidative Cyclizations in Extended Iterative Organoiron-Mediated Routes to Alkaloids. J. Org. Chem. 2012, 77, 9684. <http://dx.doi.org/10.1021/jo301617f>
  • Wang Tongen, Keyes Lauren, Patrick Brian O., Love Jennifer A.: Exploration of the Mechanism of Platinum(II)-Catalyzed C–F Activation: Characterization and Reactivity of Platinum(IV) Fluoroaryl Complexes Relevant to Catalysis. Organomettalics 2012, 31, 1397. <http://dx.doi.org/10.1021/om2007562>
  • Knölker Hans-Joachim, P. Krahl Micha, W. Schmidt Arndt: TRANSITION METALS IN ORGANIC SYNTHESIS, PART 104. IRON-MEDIATED TOTAL SYNTHESIS OF FUROCLAUSINE-A. HETEROCYCLES 2012, 86, 357. <http://dx.doi.org/10.3987/COM-12-S(N)24>
  • Forke Ronny, Gruner Konstanze K., Knott Kerstin E., Auschill Stefan, Agarwal Sameer, Martin Rene, Boehl Markus, Richter Sabine, Tsiavaliaris Georgios, Fedorov Roman: ChemInform Abstract: Transition Metals in Organic Synthesis. Part 93. Total Synthesis of Biologically Active Alkaloids Using Transition Metals. ChemInform 2011, 42, no. <http://dx.doi.org/10.1002/chin.201140232>
  • Gruner Konstanze K., Hopfmann Thomas, Matsumoto Kazuhiro, Jäger Anne, Katsuki Tsutomu, Knölker Hans-Joachim: Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids—first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (−)-trans-dihydroxygirinimbine. Org Biomol Chem 2011, 9, 2057. <http://dx.doi.org/10.1039/c0ob01088j>