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Total Synthesis of the Natural Products (±)-Symbioimine, (+)- Neosymbioimine and Formal Synthesis of Platencin

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Total Synthesis of the Natural Products (±)-Symbioimine, (+)- Neosymbioimine and Formal Synthesis of Platencin Total Synthesis of the Natural Products (±)-Symbioimine, (+)- Neosymbioimine and Formal Synthesis of Platencin. Totalsynthese der Naturstoffe (±)-Symbioimine, (+)- Neosymbioimine und Formale Synthese von Platencin. DISSERTATION der Fakultät für Chemie und Pharmazie der Eberhard-Karls-Universität Tübingen zur Erlangung des Grades eines Doktors der Naturwissenschaften 2009 vorgelegt von GEORGY N. VARSEEV Tag der mündlichen Prüfung: 19.08.2009 Dekan Prof. Dr. L. Wesemann 1. Berichterstatter: Prof. Dr. M. E. Maier 2. Berichterstatter: Prof. Dr. Th. Ziegler 3. Berichterstatter: Prof. Dr. This doctoral thesis was carried out from September 2004 to Januar 2009 at the Institut für Organische Chemie, Fakultät für Chemie und Pharmazie, Eberhard-Karls-Universität Tübingen, Germany, under the guidance of Professor Dr. Martin E. Maier. Foremost, I am indebted to Prof. Dr. Martin E. Maier, my supervisor, for his support and not only for excellent guidance during this research work but also for his confidence and many good qualities, for example, willingness always to help to solve problems. I personally thank Mr. Graeme Nicholson for HRMS, Mrs. Maria Munari for well organized supply of chemicals and her great help in the laboratory and Mrs. Egia Naiser for helping with office work. I thank all my working group members and friends for valuable discussions and their friendly nature. I would like to specially thank Dr. Anton Khartulyari, Dr. Evgeny Prusov, Dr. Viktor Vintonyak, Vaidotas Navickas, Max Wohland and Pramod Sawant. I thank Prof. Dr. V. G. Nenajdenko, Dr. V. Korotchenko and specially Dr. A. Gavryushin for teaching me chemistry and laboratory skills during my studying in Moscow. Finally, I am thankful to the love of my parents, who included so much energy into my education and cultivation of my good qualities. Publications 1. Georgy N. Varseev, Martin E. Maier “Formal Synthesis of Platencin” Angewandte Chemie 2009, 121, 3739-3742; Angewandte Chemie Int. Ed. 2009, 48, 3685-3688. 2. Georgy N. Varseev, Martin E. Maier “Enantioselective Total Synthesis of (+)- Neosymbioimine” Org. Lett. 2007, 9, 1461-1464. 3. Georgy N. Varseev, Martin E. Maier “Total Synthesis of (±)-Symbioimine” Angewandte Chemie 2006, 118, 4885-4889; Angewandte Chemie Int. Ed. 2006, 45, 4767-4771. 4. Georgy N. Varseev, Martin E. Maier “A Novel Palladium-Catalyzed Arylation- Dehydroaromatization Reaction: Synthesis of 7-Aryltetralones” Org. Lett. 2005, 7, 3881- 3884. 5. Valentine G. Nenajdenko, Georgy N. Varseev, Alexey V. Shastin and Elisabeth S. Balenkova, J. Fluorine Chem. 2005, 126, 907-913. 6. Valentine G. Nenajdenko, Georgy N. Varseev, Vasily N. Korotchenko, Alexey V. Shastin and Elisabeth S. Balenkova, J. Fluorine Chem. 2004, 124, 1339-1345. 7. Valentine G. Nenajdenko, Georgy N. Varseev, Vasily N. Korotchenko, Alexey V. Shastin and Elisabeth S. Balenkova, J. Fluorine Chem. 2003, 124, 115-118. 8. A. V. Shastin, N. V. Korotchenko, G. N. Varseev, V. G. Nenajdenko, E. S. Balenkova, Russ. J. Org. Chem. 2003, 39, 433-436. 9. Valentine G. Nenajdenko, Alexey V. Shastin, Vasily N. Korotchenko, Georgy N. Varseev, and Elisabeth S. Balenkova, Eur. J. Org. Chem. 2003, 2, 302-308. Hare Krishna Hare Krishna Krishna Krishna Hare Hare Hare Rama Hare Rama Rama Rama Hare Hare Table of Contents Table of Contents Literature Review: Biomimetic Strategies in Total Synthesis ............................................... 1 Introduction ........................................................................................................................... 1 Biomimetic Mannich, Michael and aldol reactions ............................................................... 4 Biomimetic cyclization of polyketides ................................................................................ 20 Cascade cation- cyclizations ............................................................................................. 24 Radical mediated biomimetic coupling, cyclizations and rearrangements .......................... 36 Biomimetic oxydative cyclization of polyenes (synthesis of polyethers) ........................... 43 Oxidative aromatic coupling ............................................................................................... 47 Pericyclic reactions .............................................................................................................. 52 Biomimetic [2+2] cycloaddition reactions ................................................................. 52 Biomimetic [4+2] cycloaddition reactions ................................................................. 54 6-Electrocyclization reactions .................................................................................. 76 Biomimetic Cope rearrangement ................................................................................ 78 8-Electrocyclization reactions .................................................................................. 81 Unusual electrocyclization reactions. ......................................................................... 83 Conclusion and the goal of research .................................................................................... 86 Results and Discussion ............................................................................................................ 87 1. Synthesis of spirocyclic scaffolds............................................................................... 87 2. A novel reaction for the synthesis of 7-aryltetralones ................................................ 91 3. Total synthesis of (±)-symbioimine and analogs ........................................................ 97 4. Total synthesis of (+)-neosymbioimine .................................................................... 109 5. Attempts toward the synthesis of platensimycin ...................................................... 115 6. Formal total synthesis of platencin ........................................................................... 118 7. Conclusion ................................................................................................................ 127 Experimental Section ............................................................................................................ 131 1. Synthesis of spirocyclic scaffolds............................................................................. 133 2. Synthesis of 7-aryltetralones .................................................................................... 138 3. Total synthesis of (±)-symbioimine and analogs ...................................................... 144 4. Total synthesis of (+)-neosymbioimine .................................................................... 170 5. The attempts toward the synthesis of platensimycin ................................................ 183 6. Formal total synthesis of platencin ........................................................................... 187 7. Selected NMR spectra for important compounds. ................................................... 201 Bibliography ........................................................................................................................... 255 Abbreviations Abbreviations abs. absolute Ac Acetyl AIBN Azobisisobutyronitrile aq. aqueous ar. (arom.) aromatic BBN (9-) 9-Borabicyclo[3.3.1]nonane Bn Benzyl br broad (NMR) Boc tert. Butoxy carbonyl b.p. Boiling point Bu Butyl Bz Benzoyl c Concentration CAN Cerium(IV) ammonium nitrate Cbz Carboxybenzyl COSY Correlation Spectroscopy Cp Cyclopentadienyl Cp' Pentamethylcyclopentadienyl CSA Camphor sulfonic acid Cy cyclohexyl Chemical shift in ppm (NMR) d Doublet (NMR) dba trans,trans-dibenzylideneacetone DCM Dichloromethane de Diastereomeric excess DEAD Diethyl azodicarboxylate DEPT Distortionless Enhancement by Polarization Transfer DIAD Di-iso-propyl azodicarboxylate DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone DIBAL(-H) Diisobutylaluminium hydride Abbreviations DMAP 4-Dimethylaminopyridine DME Dimethoxyethane DMF N,N-Dimethylformamide DMP Dess-Martin periodinane DMSO Dimethylsulfoxide dr Diastereomeric ratio dppf 1,1’-Bis(diphenylphosphino)ferrocene E trans ee Enantiomeric excess EI Electron impact EOM Ethoxymethoxymethyl Eq. equation ESI Electronspray ionization Et Ethyl Et2O Diethyl ether EtOAc Ethyl acetate Fig. Figure Fur Furyl g gram(s) GC Gas chromatography h hour(s) HOMO Highest occupied molecular orbital HPLC high performance liquid chromatography HRMS high resolution mass spectrometry Hz Hertz IBX 2-Iodoxybenzoic acid IC50 half maximal Inhibitory Concentration IR Infrared PCC Pyridinium chlorochromate Piv Pivaloyl iPr isopropyl J coupling constant Abbreviations L liter(s) LA Lewis acid LC Liquid chromatography LDA Lithium diisopropylamide HMDS Hexamethyldisilazane LUMO Lowest unoccupied molecular orbital m Multiplet (NMR) mCPBA meta-cloroperbenzoic acid Me Methyl MeOH Methanol mg milligram g microgram MOM Methoxymethyl Ms Methanesulfonyl MVK Methylvinylketone m/z Mass to charge ratio (MS) NBS N-bromosuccinimide nM nanomolar NMO N-Methylmorpholin-N-Oxide NMR Nuclear magnetic resonance NOESY Nuclear Overhauser Effect Spectroscopy Ph Phenyl PMB p-Methoxybenzyl PMP p-Methoxyphenyl PPTS Pyridinium para-toluene sulfonate pTSA para-Toluene sulfonic acid Py Pyridine q Quartet (NMR) RCM Ring-closing metathesis Rf Retention factor (TLC) rt Room temperature (ca. 23 °C) s Singlet (NMR) Abbreviations SET Single electron transfer t Triplet (NMR) TBAB Tetrabutylammonium bromide TBAF Tetrabutylammonium fluoride TBS tert-Butyldimethylsilyl TCAA Trichloroacetanhydride
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