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1. Total synthesis of the Schisandraceae nortriterpenoid rubriflordilactone A

Author

Anderson, EA, Chaubet, G, Goh, S, Mohammad, M, Gockel, B, Cordonnier, MC, Baars, H, and Phillips, A

Abstract

Full details of the total synthesis of the Schisandraceae nortriterpenoid natural product rubriflordilactone A are reported. Palladium- and cobalt-catalyzed polycyclizations were employed as key strategies to construct the central pentasubstituted arene from bromoendiyne and triyne precursors. This required the independent assembly of two AB ring aldehydes for combination with a common diyne component. A number of model systems were explored to investigate these two methodologies, and also to establish routes for the installation of the challenging benzopyran and butenolide rings.

Published
2017
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2. Corrigendum: MTH1 inhibition eradicates cancer by preventing sanitation of the dNTP pool.

Author

Gad H, Koolmeister T, Jemth AS, Eshtad S, Jacques SA, Ström CE, Svensson LM, Schultz N, Lundbäck T, Einarsdottir BO, Saleh A, Göktürk C, Baranczewski P, Svensson R, Berntsson RP, Gustafsson R, Strömberg K, Sanjiv K, Jacques-Cordonnier MC, Desroses M, Gustavsson AL, Olofsson R, Johansson F, Homan EJ, Loseva O, Bräutigam L, Johansson L, Höglund A, Hagenkort A, Pham T, Altun M, Gaugaz FZ, Vikingsson S, Evers B, Henriksson M, Vallin KSA, Wallner OA, Hammarström LGJ, Wiita E, Almlöf I, Kalderén C, Axelsson H, Djureinovic T, Carreras Puigvert J, Häggblad M, Jeppsson F, Martens U, Lundin C, Lundgren B, Granelli I, Jenmalm Jensen A, Artursson P, Nilsson JA, Stenmark P, and Scobie M

Published
2017
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3. Total Synthesis of (+)-Rubriflordilactone A.

Author

Goh SS, Chaubet G, Gockel B, Cordonnier MC, Baars H, Phillips AW, and Anderson EA

Subjects
Biological Products chemistry, Catalysis, Cobalt chemistry, Cyclization, Kadsura chemistry, Palladium chemistry, Schisandra chemistry, Stereoisomerism, Triterpenes chemistry, Biological Products chemical synthesis, Triterpenes chemical synthesis
Abstract

Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to form the CDE rings, and converge on a late-stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products., (© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.)

Published
2015
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4. MTH1 inhibition eradicates cancer by preventing sanitation of the dNTP pool.

Author

Gad H, Koolmeister T, Jemth AS, Eshtad S, Jacques SA, Ström CE, Svensson LM, Schultz N, Lundbäck T, Einarsdottir BO, Saleh A, Göktürk C, Baranczewski P, Svensson R, Berntsson RP, Gustafsson R, Strömberg K, Sanjiv K, Jacques-Cordonnier MC, Desroses M, Gustavsson AL, Olofsson R, Johansson F, Homan EJ, Loseva O, Bräutigam L, Johansson L, Höglund A, Hagenkort A, Pham T, Altun M, Gaugaz FZ, Vikingsson S, Evers B, Henriksson M, Vallin KS, Wallner OA, Hammarström LG, Wiita E, Almlöf I, Kalderén C, Axelsson H, Djureinovic T, Puigvert JC, Häggblad M, Jeppsson F, Martens U, Lundin C, Lundgren B, Granelli I, Jensen AJ, Artursson P, Nilsson JA, Stenmark P, Scobie M, Berglund UW, and Helleday T

Subjects
Animals, Catalytic Domain, Cell Death drug effects, Cell Survival drug effects, Crystallization, DNA Damage, DNA Repair Enzymes chemistry, DNA Repair Enzymes metabolism, Deoxyguanine Nucleotides metabolism, Enzyme Inhibitors chemistry, Enzyme Inhibitors pharmacokinetics, Enzyme Inhibitors pharmacology, Enzyme Inhibitors therapeutic use, Female, Humans, Male, Mice, Models, Molecular, Molecular Conformation, Molecular Targeted Therapy, Neoplasms pathology, Oxidation-Reduction drug effects, Phosphoric Monoester Hydrolases chemistry, Phosphoric Monoester Hydrolases metabolism, Pyrimidines chemistry, Pyrimidines pharmacokinetics, Pyrimidines pharmacology, Pyrimidines therapeutic use, Pyrophosphatases antagonists & inhibitors, Reproducibility of Results, Xenograft Model Antitumor Assays, Nudix Hydrolases, DNA Repair Enzymes antagonists & inhibitors, Neoplasms drug therapy, Neoplasms metabolism, Nucleotides metabolism, Phosphoric Monoester Hydrolases antagonists & inhibitors
Abstract

Cancers have dysfunctional redox regulation resulting in reactive oxygen species production, damaging both DNA and free dNTPs. The MTH1 protein sanitizes oxidized dNTP pools to prevent incorporation of damaged bases during DNA replication. Although MTH1 is non-essential in normal cells, we show that cancer cells require MTH1 activity to avoid incorporation of oxidized dNTPs, resulting in DNA damage and cell death. We validate MTH1 as an anticancer target in vivo and describe small molecules TH287 and TH588 as first-in-class nudix hydrolase family inhibitors that potently and selectively engage and inhibit the MTH1 protein in cells. Protein co-crystal structures demonstrate that the inhibitors bind in the active site of MTH1. The inhibitors cause incorporation of oxidized dNTPs in cancer cells, leading to DNA damage, cytotoxicity and therapeutic responses in patient-derived mouse xenografts. This study exemplifies the non-oncogene addiction concept for anticancer treatment and validates MTH1 as being cancer phenotypic lethal.

Published
2014
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5. A palladium-mediated cascade cyclisation approach to the CDE cores of rubriflordilactone A and lancifodilactone G.

Author

Cordonnier MC, Kan SB, and Anderson EA

Subjects
Anti-HIV Agents chemistry, Anti-HIV Agents pharmacology, Catalysis, Cyclization, Triterpenes chemistry, Triterpenes pharmacology, Anti-HIV Agents chemical synthesis, Palladium chemistry, Triterpenes chemical synthesis
Abstract

Palladium-mediated cascade cyclisation reactions have been applied to the synthesis of the CDE-ring cores of two anti-HIV natural products, rubriflordilactone A and lancifodilactone G.

Published
2008
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