Synthesis of Natural Products and Analogues
Synthesis of Natural Products and Analogues
Publications
| • | D. Gladow, S. Senf, J. Wiecko, D. Lentz, R. Zimmer, H.-U. Reißig* New Trifluoromethyl-Substituted Heterocycles by Multicomponent Reactions of Siloxycyclopropanes Chem. Heterocycl. Compd. 2017, 53, 416 – 421. |
| • | M. Wilsdorf*, S. Sörgel, H.-U. Reißig* Lessons Learned During Spiroketalization Experiments – Progress and Setbacks in the Preparation of Oxygenated Rubromycins and Synthesis of 3´-Desoxyheliquino-mycinone Eur. J. Org. Chem. 2016, 5757 – 5769. |
| • | M. Wilsdorf*, H.-U. Reißig* Towards γ-Rubromycin: Model Studies, Development of a New C3 Building Block and Synthesis of 4´-Silyl-γ-rubromycin Eur. J. Org. Chem. 2016, 5747 – 5756. |
| • | M. Wilsdorf, H.-U. Reißig* Model Studies towards New Functionalized Bisbenzannulated [5,6]-Spiroketals Eur. J. Org. Chem. 2016, 1555–1561. |
| • | M. Jasiński*, G. Utecht, A. Fruziński, H.-U. Reißig Three-Step Synthesis of 3-Aminoseptanoside Derivatives Using Lithiated Methoxyallene and δ-Siloxynitrones Synthesis 2016, 48, 893 – 905. |
| • | H. R. A. Golf, A. M. Oltmanns, D. H. Trieu, H.-U. Reissig,* A. Wiehe* Synthesis of Functionalized BODIPYs, BODIPY-Corrole, and BODIPY-Porphyrin Arrays with 1,2,3-Triazole Linkers Using the 4-Azido(tetrafluorophenyl)-BODIPY Building Block Eur. J. Org. Chem. 2015, 4224 – 4237. |
| • | C. Beemelmanns, H.-U. Reissig* Strychnine as Target, Samarium Diiodide as Tool: A Personal Story Chem. Rec. 2015, 15, 872 – 885. |
| • | H. R. A. Golf, H.-U. Reissig*, A. Wiehe* Synthesis of SF5-Substituted Tetrapyrroles, Metalloporphyrins, BODIPYs, and Their Dipyrrane Precursors J. Org. Chem. 2015, 80, 5133 – 5143. |
| • | C. Beemelmanns, H.-U. Reissig* Evolution of a Short Route to Strychnine by Using the Samarium-Diiodide-Induced Cascade Cyclization as a Key Step Chem. Eur. J. 2015, 21, 8416 – 8425. |
| • | H. R. A. Golf, H.-U. Reißig*, A. Wiehe* Nucleophilic Substitution on (Pentafluorophenyl)dipyrromethane: A New Route to Building Blocks for Functionalized BODIPYs and Tetrapyrroles Org. Lett. 2015, 17, 982 – 985. |
| • | H. R. A. Golf, H.-U. Reißig, A. Wiehe* Regioselective Nucleophilic Aromatic Substitution Reaction of meso-Pentafluorophenyl-Substituted Porphyrinoids with Alcohols Eur. J. Org. Chem. 2015, 1548 – 1568. |
| • | C. N. Rao, D. Lentz, H.-U. Reißig* Synthese polycyclischer tertiärer Carbinamine durch Samariumdiiodid-vermittelte Cyclisierungen von Indolylsulfinylimien Angew. Chem. 2015, 127, 2788 – 2792. C. N. Rao, D. Lentz, H.-U. Reißig* Synthesis of Polycyclic Tertiary Carbinamines by Samarium Diiodide Mediated Cyclizations of Indolyl Sulfinyl Imines Angew. Chem. Int. Ed. 2015, 54, 2750 – 2753. |
| • | M. Wilsdorf, H.-U. Reißig* Eine konvergente Totalsynthese des Telomerase-Inhibitors (±)-γ-Rubromycin Angew. Chem. 2014, 126, 4420 – 4424. M. Wilsdorf, H.-U. Reißig* A Convergent Total Synthesis of the Telomerase Inhibitor (±)-γ-Rubromycin Angew. Chem. Int. Ed. 2014, 53, 4332 – 4336. |
| • | M. Jasiński, E. Moreno-Clavijo, H.-U. Reißig* Synthesis of a Series of Enantiopure Polyhydroxylated Bicyclic N-Heterocycles from an l-Erythrose Derived Nitrone and Alkoxyallenes Eur. J. Org. Chem. 2014, 442 – 454. |
| • | C. Beemelmanns, S. Gross, H.-U. Reißig* Towards the Core Structure of Strychnos Alkaloids Using Samarium Diiodide-Induced Reactions of Indole Derivatives Chem. Eur. J. 2013,19, 17801 – 17808. |
| • | V. M. Schmiedel, S. Stefani, H.-U. Reißig* Stereodivergent Synthesis of Jaspine B and its Isomers using a Carbohydrate-derived Alkoxyallene as C3-building Block |
| • | T. H. Ngo, H. Berndt, M. Wilsdorf, D. Lentz, H.-U. Reißig* Linear and Cyclic Hybrids of Alternating Thiophene–Amino Acid Units: Synthesis and Effects of Chirality on Conformation and Molecular Packing
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C. Parmeggiani, F. Cardona, L. Giusti, H.-U. Reißig*, A. Goti
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| • | M. H. Beyzavi, C. Nietzold, H.-U. Reißig*, A. Wiehe* Synthesis of Functionalized trans-A2B2-Porphyrins Using Donor-Acceptor Cyclopropane-Derived Dipyrromethanes Adv. Synth. Catal. 2013, 355, 1409 – 1422. |
| • | M. Wilsdorf, D. Leichnitz, H.-U. Reißig* Trifluoromethanesulfonic Acid Catalyzed Friedel-Crafts Alkylations of 1,2,4-Trimethoxybenzene with Aldehydes or Benzylic Alcohols Org. Lett. 2013, 15, 2494 – 2497. |
| • | M. H. Beyzavi, D. Lentz, H.-U. Reißig*, A. Wiehe* Synthesis of New Functionalized Calix[n]phyrin Macrocycles with Varied Ring Sizes by Using a Sterically Congested Dipyrromethane Chem. Eur. J. 2013, 19, 6203 – 6208. |
| • | T. H. Ngo, H. Berndt, D. Lentz, H.-U. Reißig* Linear and Cyclic Amides with a Thiophene Backbone: Ultrasound-Promoted Synthesis and Crystal Structures J. Org. Chem. 2012, 77, 9676 – 9683. |
| • | M. Wilsdorf, H.-U. Reißig* Einfach und dennoch herausfordernd: Neues zur asymmetrischen Synthese von Spiroketalen Angew. Chem. 2012, 124, 9624 – 9626. M. Wilsdorf, H.-U. Reißig* Simple, but Challenging: Recent Developments in the Asymmetric Synthesis of Spiroketals Angew. Chem. Int. Ed. 2012, 51, 9486 – 9488. |
| • | M. Jasiński, Dieter Lentz, E. Moreno-Clavijo, H.-U. Reißig* Application of L-Erythrose-Derived Nitrones in the Synthesis of Polyhydroxylated Compounds via 3,6-Dihydro-2H-1,2-oxazine Derivatives Eur. J. Org. Chem. 2012, 3304 – 3316. |
| • | M. Jasiński, Dieter Lentz, H.-U. Reißig* Carbohydrate-Auxiliary Assisted Preparation of Enantiopure 1,2-Oxazine Derivatives and Aminopolyols Beilstein J. Org. Chem. 2012, 8, 662-674. |
| • | L. Bouché, H.-U. Reißig* Synthesis of Novel Carbohydrate Mimetics via 1,2-Oxazines Pure Appl. Chem. 2012, 84, 23 – 36. |
| • | C. Beemelmanns, D. Lentz, H.-U. Reißig* Samarium Diiodide Induced Cyclizations of γ-, δ- and ε-Indolyl Ketones: Reductive Coupling, Intermolecular Trapping, and Subsequent Transformations of Indolines Chem. Eur. J. 2011, 17, 9720 – 9730. |
| • | V. Dekaris, R. Pulz, A. Al-Harrasi, D. Lentz, H.-U. Reißig* Stereoselective Synthesis of Aza, Amino and Imion Sugar Derivatives by Hydroboration of 3,6-Dihydro-2H-1,2-oxazines as Key Reaction Eur. J. Org. Chem. 2011, 3210 – 3219. |
| • | C. Beemelmanns, H.-U. Reißig* Samarium diiodide induced ketyl-(het)arene cyclisations towards novel N-heterocycles Chem. Soc. Rev., 2011, 40, 2199 – 2210. |
| • | H. Özbek, D. Lentz, H.-U. Reißig* New Macrocyclic Peptidomimetics Containing 5-Aminothiophene Subunits Eur. J. Org. Chem. 2010, 6319 – 6322. |
| • | M. Brasholz, B. Dugovič , H.-U. Reißig* 3-Alkoxy-2,5-dihydrofurans by Gold-Catalyzed Allenyl Cyclizations and Their Transformation into 1,4-Dicarbonyl Compounds, Cyclopentenones, and Butenolides Synthesis 2010, 3855 – 3864. |
| • | C. Beemelmanns, H.-U. Reißig* Eine kurze formale Strychnin-Totalsynthese mit einer Samariumdiiodid-induzierten Kaskadenreaktion als Schlüsselschritt Angew. Chem. 2010, 122, 8195 – 8199. C. Beemelmanns, H.-U. Reißig* A Short Formal Total Synthesis of Strychnine with a Samarium Diiodide Induced Cascade Reaction as the Key Step Angew. Chem. Int. Ed. 2010, 49, 8021 – 8025. |
| • | F. Pfrengle, H.-U. Reißig* Internally Protected Amino Sugar Equivalents from Enantiopure 1,2-Oxazines: Synthesis of Variably Configured Carbohydrates with C-Branched Amino Sugar Units Chem. Eur. J. 2010, 16, 11915 – 11925. |
| • | A. Schwanke, C. Murruzzu, B. Zdrazil. R. Zuhse, M. Natek, M. Höltje, H. C. Korting, H.-U. Reißig, H.-D. Höltje, M. Schäfer-Korting* Antitumor Effects of Guanosine-Analog Phosphonates Identified by Molecular Modelling Int. J. Pharm. 2010, 397, 9 – 18. |
| • | U. K. Wefelscheid, H.-U. Reißig* Synthesis of New Steroid Analogues by Samarium Diiodide Induced Cyclisations of γ-Naphthyl 1,3-Diones Tetrahedron: Asymmetry 2010, 21, 1601 – 1610. |
| • | F. Pfrengle, H.-U. Reißig* Addition of Lithiated Enol Ethers to Nitrones and Subsequent Lewis Acid Induced Cyclizations to Enantiopure 3,6-Dihydro-2H-pyrans – an Approach to Carbohydrate Mimetics Beilstein Journal of Organic Chemistry 2010, 6, No. 75. |
| • | M. Höltje, A. Richartz, B. Zdrazil, A. Schwanke, B. Dugovič, C. Murruzzu, H.-U. Reißig, H. C. Korting, B. Kleuser, H.-D. Höltje, M. Schäfer-Korting* Human Polymerase α-Inhibitors for Skin Tumors. Part 2. Modeling, Synthesis and Influence on Normal and Transformed Keratinocytes of New Thymidine and Purine Derivatives J. Enzym. Inhib. Med. Chem., 2010, 25 (2), 250-265. |
| • | V. Dekaris, H.-U. Reißig* Stereocontrolled Syntheses of Enantiopure Polyhydroxylated Azetidines via 1,2-Oxazines Synlett 2010, 42 – 46. |
| • | F. Pfrengle, D. Lentz, H.-U. Reißig* A New Ring Closure Approach to Enantiopure 3,6-Dihydro-2H-pyrans: Stereodivergent Access to Carbohydrate Mimetics Org. Lett. 2009, 11, 5534 – 5537. |
| • | V. Prisyazhnyuk, M. Jachan, I. Brüdgam, R. Zimmer, H.-U. Reißig* Addition of Lithiated Methoxyallene to Aziridines – A Novel Access to Enantiopure Piperidine and β-Amino Acid Derivatives Collect. Czech. Chem. Commun, 2009, 74, 1069 – 1080. |
| • | M. Brasholz, H.-U. Reißig* Alkoxyallene-Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L-Cymarose, L-Sarmentose, L-Diginose and L-Oleandrose Eur. J. Org. Chem. 2009, 3595– 3604. |
| • | J. Dash, H.-U. Reißig* A New and Flexible Synthesis of 4-Hydroxypyridines: Rapid Access to Caerulomycins A, E and Functionalized Terpyridines Chem. Eur. J. 2009, 15, 6811 – 6814. |
| • | F. Pfrengle, D. Lentz, H.-U. Reißig* Stereodivergente De-novo-Synthese verzweigter Aminozucker durch Lewis-Säure-induzierte Umlagerung von 1,2-Oxazinen Angew. Chem. 2009, 121, 3211 - 3215. |
| F. Pfrengle, D. Lentz, H.-U. Reißig* Stereodivergent De novo Synthesis of Branched Amino Sugars by Lewis Acid promoted Rearrangement of 1,2-Oxazines Angew. Chem. Int. Ed. 2009, 48, 3165 - 3169. |
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| • | V. Blot, U. Jacquemard, H.-U. Reißig,* B. Kleuser Practical Syntheses of Sphingosine-1-Phosphate and Analogues Synthesis 2009, 759 – 766. |
| • | J. Dernedde, S. Enders, H.-U. Reißig, M. Roskamp, S. Schlecht,* S. Yekta Inhibition of selectin binding by colloidal gold with functionalized shells Chem. Commun. 2009, 932 – 934. |
| • | B. Bressel, H.-U. Reißig* A New Approach to Neuraminic Acid Analogues via 1,2-Oxazines Org. Lett. 2009, 11, 527 – 530. |
| • | M. Brasholz, H.-U. Reißig,* R. Zimmer Sugars, Alkaloids and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes Acc. Chem. Res. 2009, 42, 45– 56. |
| • | C. Venkatesh, H.-U. Reißig* Model Studies for the Synthesis of Heliquinomycin: Preparation of New Spiroketals Synthesis 2008, 3605 – 3614. |
| • | F. Aulenta, U. K. Wefelsched, I. Brüdgam, H.-U. Reißig* Nitrogen-Containing Tricyclic and Tetracyclic Compounds via Stereoselective Samarium Diiodide Promoted Cyclizations of Quinolyl-Substituted Ketones – A New Access to Azasteroids Eur. J. Org. Chem. 2008, 2325 - 2335. |
| • | U. K. Wefelscheid, H.-U. Reißig* Pentacyclic Compounds by Samarium Diiodide-Induced Cascade Cyclizations of Naphthyl-Substituted 1,3-Diones Adv. Synth. Catal, 2008, 250, 65 – 69. |
| • | M. Brasholz, S. Sörgel, C. Azap, H.-U. Reißig* Rubromycins: Structurally Intriguing, Biologically Valuable, Synthetically Challenging Antitumour Antibiotics Eur. J. Org. Chem. 2007, 3801 – 3814. |
| • | F. Aulenta, M. Berndt, I. Brüdgam, H. Hartl, S. Sörgel, H.-U. Reißig* A New, Efficient and Stereoselective Synthesis of Tricyclic and Tetracyclic Compounds by Samarium Diiodide Induced Cyclisations of Naphthyl-Substituted Arylketones – An Easy Access to Steroid-Like Skeletons Chem. Eur. J. 2007, 13, 6047 – 6062. |
| • | S. Sörgel, I. Brüdgam, H. Hartl, H.-U. Reißig* Crystal structure of 2-bromo-1,4,5,7,8-pentamethoxynaphthalene, C10H2Br(OCH3)5 Z. Kristallogr. NCS 2006, 221, 278 – 280. |
| • | S. Sörgel, C. Azap, H.-U. Reißig Synthesis of Bisbenzannulated Spiroketals – Model Studies for a Modular Approach to Rubromycins Org. Lett. 2006, 8, 4875 – 4878. |
| • | S. Kaden, H.-U. Reißig* Efficient Approach to the Azaspirane Core of FR 901483 Org. Lett. 2006, 8, 4763 – 4766. |
| • | S. Sörgel, C. Azap, H.-U. Reißig* Preparation of Highly Alkoxy-Substituted Naphthaldehyde Derivatives – A Regioselective Approach to Building Blocks for the Synthesis of Rubromycins Eur. J. Org. Chem. 2006, 4405 – 4418. |
| • | M. A. Chowdhury, H.-U. Reißig* Syntheses of Highly Substituted Furan and Pyrrole Derivatives via Lithiated 3-Aryl-1-methoxyallenes: Application to the Synthesis of Codonopsinine. Synlett 2006, 2383 – 2386. |
| • | M. Brasholz*, X. Luan, H.-U. Reißig Towards the Rubromycins: An Efficient Synthesis of a Suitable Isocoumarin Precursor, its Lactam Analogue, and Palladium-Catalyzed Couplings Synthesis 2005, 3571 – 3580. |
| • | S. Kaden, M. Brockmann, H.-U. Reißig* Synthesis of Enantiopure 2-Substituted Pyrrolidin-3-ones via Lithiated Alkoxyallenes – An Auxilary Based Synthesis of Both Enantiomers of the Antibiotic Anisomycin. Helv. Chim. Acta 2005, 88, 1826 – 1838. |
| • | M. Brasholz, H.-U. Reißig* An Expedient and Short Synthesis of a 6-Iodo Isocoumarin Building Block for the Rubromycin Family and its First Palladium-Catalyzed Couplings Synlett 2004, 2736 – 2738. |
| • | M. Berndt, I. Hlobilová, H.-U. Reißig* Stereoselective Formation of Tri- and Tetracycles by Samarium Diiodide-Induced Cyclizations of Naphthyl-Substituted Ketones Org. Lett. 2004, 6, 957 – 960. > |
| • | O. Flögel, M. G. Okala Amombo, H.-U. Reißig*, G. Zahn, I. Brüdgam, H. Hartl A Stereoselective and Short Total Synthesis of the Polyhydroxylated γ-Amino Acid (-)-Detoxinine Based on Stereoselective Preparation of Dihydropyrrole Derivatives from Lithiated Alkoxyallenes Chem. Eur. J. 2003, 9, 1405 – 1415. |
| • | W. Schade, H.-U. Reißig* Stereocontrolled Synthesis of the Taxol C-13 Side Chain: Methyl (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenylpropanoate J. Prakt. Chem. 1999, 341, 685 – 686. |
| • | J. Schnaubelt, B. Frey, H.-U. Reißig* Formal Total Synthesis of (+)-Dihydromevinolin via a Chelate-Controlled Intramolecular Diels-Alder Reaction as the Key Step Helv. Chim. Acta 1999, 82, 666 – 676. |
| • | H. Angert, R. Czerwonka, H.-U. Reißig* Additions of Silyl Enol Ethers to β-Formyl Esters – A Chelate-Controlled Synthesis of the Pheromone (+)-Eldanolide. Liebigs Ann. 1996, 259 – 263. |
| • | K. Paulini, H.-U. Reißig* Preparation of Novel Lipophilic GABA-Analogues Containing Cyclopropane Rings via Cyclopropanation of N-Silylated Unsaturated Amines J. prakt. Chem. 1995, 337, 55 – 59. |
| • | K. Paulini, H.-U. Reißig* Synthesis of Dipeptides Containing Novel Cyclopropyl- and Cyclopropenyl-Substituted β- und γ-Amino Acids Liebigs Ann. Chem. 1994, 549 – 554. |
| • | A. G. Beck-Sickinger*, E. Hoffmann, K. Paulini, H.-U. Reißig, K.-D. Willim, H. A. Wieland, G. Jung High-Affinity Analogues of Neuropeptide Y Containing Conformationally Restricted Non-Proteinogenic Amino Acids Biochem. Soc. Trans. 1994, 22, 145 – 149. |
| • | J. Schnaubelt, R. Zschiesche, H.-U. Reißig*, H. J. Lindner, J. Richter Synthese von Östronderivaten aus Siloxycyclopropancarbonsäureestern Liebigs Ann. Chem. 1993, 61 – 70. |
| • | K. Paulini, H.-U. Reißig* Efficient Synthesis of a Novel GABA Analogue Incorporating a Cyclopropene Ring Synlett 1992, 505 – 506. |
| • | R. Zschiesche, T. Hafner, H.-U. Reißig* Conversion of Polyfunctional Nitroalkanes into Carbonyl Compounds – Synthesis of the Pheromone Chalcogran and of Key Building Blocks for the Macrolides Pyrenophorin and Vermiculine Liebigs Ann. Chem. 1988, 1169 – 1173. |
| • | R. Zschiesche, H.-U. Reißig* Eine Synthexe von rac-Norbisabolid Liebigs Ann. Chem. 1987, 387 - 388. |
| • | I. Reichelt, H.-U. Reißig* Neue Chrysanthemumsäurederivative druch Deprotonierung-Alkylierung Liebigs Ann. Chem. 1985, 650 - 652. |