Browsing by Author "Myers, Andrew"
Now showing items 1-20 of 41
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Allene Synthesis from 2-Alkyn-1-Ols
Myers, Andrew; Finney, Nathaniel S.; Kuo, Elaine Y. (Elsevier, 1989)Activation of 2-alkyn-1-01s as their methanesulfonate esters and displacement with hydrazine urnishes the corresponding alkynyl hydrazine derivatives which undergo smooth oxidative rearrangement with diethyl azodicarboxylate ... -
Anti-proliferative activity of the NPM1 interacting natural product avrainvillamide in acute myeloid leukemia
Andresen, Vibeke; Erikstein, Bjarte S; Mukherjee, Herschel; Sulen, André; Popa, Mihaela; Sørnes, Steinar; Reikvam, Håkon; Chan, Kok-Ping; Hovland, Randi; McCormack, Emmet; Bruserud, Øystein; Myers, Andrew G; Gjertsen, Bjørn T (Nature Publishing Group, 2016)Mutated nucleophosmin 1 (NPM1) acts as a proto-oncogene and is present in ~30% of patients with acute myeloid leukemia (AML). Here we examined the in vitro and in vivo anti-leukemic activity of the NPM1 and chromosome ... -
A Chiral N-Crotonyloxazolidinone Diels-Alder Adduct
Marsh, Richard E.; Schaefer, William P.; Kukkola, Paivi J.; Myers, Andrew (International Union of Crystallography, 1992)(4S)-4-Benzyl-3-[(4S,5S)-(1-methoxy-5-methylcyclohexen-4-yl) carbonyl]-2-oxazolidinone, C<sub>19</sub>H<sub>23</sub>NO<sub>4</sub>, <i>M</i>,=329.40, monoclinic, <i>P</i>2<sub>1</sub>, <i>a</i>=11.453(3), <i>b</i>=7.163(4), ... -
Component-Based Syntheses of Trioxacarcin A, DC-45-A1, and Structural Analogs
Magauer, Thomas; Smaltz, Daniel J.; Myers, Andrew G. (2014)The trioxacarcins are polyoxygenated, structurally complex natural products that potently inhibit the growth of cultured human cancer cells. Here we describe syntheses of trioxacarcin A, DC-45-A1, and structural analogs ... -
Component-Based Syntheses of Trioxacarcins
Smaltz, Daniel Jonathan (2014-06-06)The trioxacarcins are structurally complex, highly oxygenated bacterial isolates that potently inhibit the growth of human cancer cells in culture as a consequence of their ability to alkylate guanosine residues of duplex ... -
A Concise Synthesis of the Naphthoic Acid Component of Neocarzinostatin Chromophore Featuring a New Photocyclization Reaction
Myers, Andrew; Subramanian, Vijaya; Hammond, Marlys (Elsevier, 1995)A 6-step synthesis of the naphthoic acid component of the natural antitumor agent neocarzinostatin chromophore is described. The synthetic route employs a 4-bromo-3-methylanisole as the starting material, proceeds in 31-37% ... -
Constitution of Antheridium-Inducing Factor of Anemia Phyllitidis
Corey, E. J.; Myers, Andrew G.; Takahashi, Nobutaka; Yamane, Hisakazu; Schraudolf, Helmut (Elsevier, 1986)Careful comparison of naturally derived and synthetic samples of the antheridium-inducing factor of Anemia phyllitidis, AA,,, by TLC, HPLC, NMR and GC-MS measurements allow unambiguous assignment of structure 2 to this ... -
Crystal Structure of Neocarzinostatin, an Antitumor Protein-Chromophore Complex
Kim, Kyoung-Hee; Kwon, Byoung-Mog; Myers, Andrew; Rees, Douglas (American Association for the Advancement of Science, 1993)Structures of the protein-chromophore complex and the apoprotein form of neocarzinostatin were determined at 1.8 angstrom resolution. Neocarzinostatin is composed of a labile chromophore with DNA-cleaving activity and a ... -
Diastereoselective Additions of Allylmetal Reagents to Free and Protectedsyn-?,?-Dihydroxyketones Enable Efficient Synthetic Routes to Methyl Trioxacarcinoside A
Smaltz, Daniel Jonathan; Svenda, Jakub; Myers, Andrew G. (American Chemical Society (ACS), 2012)Two routes to the 2,6-dideoxysugar methyl trioxacarcinoside A are described. Each was enabled by an apparent α-chelation-controlled addition of an allylmetal reagent to a ketone substrate containing a free α-hydroxyl group ... -
Direct Transformation of 2,3-Epoxy Alcohols into Hydroxy Carbonates Under Mildly Basic Conditions
Myers, Andrew; Widdowson, Katherine L. (Elsevier, 1988)2,3-Epoxy alcohols are transformed into the corresponding C2-inverted hydroxy carbonates upon treatment with cesium carbonate-powdered 3-A molecular sieves in N,N-dimethylformamide under one atmosphere of carbon dioxide ... -
An Efficient Directed Claisen Reaction Allows for Rapid Construction of 5,6-Disubstituted 1,3-Dioxin-4-ones
Myers, Andrew G.; Ziyang Zhang, Yoshiaki (Thieme Publishing Group, 2015)An efficient directed Claisen reaction between tert-butyl propionate and phenyl propionate is described. This enables a practical synthesis of 6-ethyl-2,2,5-trimethyl-4H-1,3-dioxin-4-one and thereby (Z)-[(4-ethylidene-2, ... -
Efficient Synthesis and Intramolecular Cyclopropanation of Unsaturated Diazoacetic Esters
Corey, Elias; Myers, Andrew (Elsevier, 1984)New and efficient procedures are described for the conversion of homoallylic alcohols to esters of diazoacetic acid and for the further intramolecular cyclopropanation of those esters. -
I. Synthesis of C4-Modified Tetracyclines II. Aldolizations of Pseudoephenamine Glycinamide and Applications Toward the Synthesis of Monocyclic β-Lactam Antibiotics
Sussman, Robin Judith (2015-05-14)Part one of this thesis describes the production of C4-modified tetracycline derivatives. Our synthetic strategy originally targeted SF2575, a C4-oxygenated tetracycline analog with antiproliferative properties, but was ... -
An Improved Preparation of Highly Enantiomerically Enriched (R)-(+)-4-tert-Butyldimethylsiloxy-2-cyclopenten-1-one.
Myers, Andrew; Hammond, Marlys; Wu, Yusheng (Elsevier, 1996)A convenient procedure for the preparation of the title compound of >=99% ee is presented as well as simple analytical methods for the determination of the optical purity of the intermediates in the sequence. -
Lithium Amidotrihydroborate, a Powerful New Reductant. Transformation of Tertiary Amides to Primary Alcohols.
Myers, Andrew G.; Yang, Bryant H.; Kopecky, David J. (Elsevier Science Ltd, 1996)Lithium amidotrihydroborate (LiH3NBH3, LAB) is a new and highly nucleophilic reducing agent that is easily prepared by deprotonation of the commercial reagent borane-ammonia complex (H3NBH3) with n-BuLi in tetrahydrofuran ... -
Mediator Kinase Inhibition Further Activates Super-Enhancer Associated Genes in AML
Pelish, Henry E.; Liau, Brian B.; Nitulescu, Ioana I.; Tangpeerachaikul, Anupong; Poss, Zachary C.; Da Silva, Diogo H.; Caruso, Brittany T.; Arefolov, Alexander; Fadeyi, Olugbeminiyi; Christie, Amanda L.; Du, Karrie; Banka, Deepti; Schneider, Elisabeth V.; Jestel, Anja; Zou, Ge; Si, Chong; Ebmeier, Christopher C.; Bronson, Roderick T.; Krivtsov, Andrei V.; Myers, Andrew G.; Kohl, Nancy E.; Kung, Andrew L.; Armstrong, Scott A.; Lemieux, Madeleine E.; Taatjes, Dylan J.; Shair, Matthew D. (2015)Super-enhancers (SEs), which are composed of large clusters of enhancers densely loaded with the Mediator complex, transcription factors (TFs), and chromatin regulators, drive high expression of genes implicated in cell ... -
A Method for the Preparation of Differentiated \(trans\)-1,2-Diol Derivatives with Enantio- and Diastereocontrol
Lim, Sang Min; Hill, Nicholas; Myers, Andrew G. (American Chemical Society, 2009)We describe a synthetic sequence that allows for the preparation of optically active \(trans\)-1,2-diol monosilyl ether derivatives from ketones, providing a new means for retrosynthetic simplification of differentiated ... -
Mild Conditions for the Removal of Acid-Labile Protective Groups
Myers, Andrew; Fundy, Marry Ann M.; Lindstrom, Peter A. Jr (Elvesier, 1988)Hydrogen peroxide-trichloroacetic acid is an effective reagent combination for the mild cleavage of acid-labile protective groups. -
Multiplicative Expansion of the Pool of Fully Synthetic Tetracycline Antibiotics
Wright, Peter Maughan (2013-03-05)This thesis describes the development of chemical pathways for the preparation of more than 80 novel fully synthetic tetracyclines with structural variability at positions C5 and C5a. Progress toward the synthesis of ... -
A Multiply Convergent Platform for the Synthesis of Trioxacarcins
Švenda, Jakub; Hill, Nicholas; Myers, Andrew G. (United States National Academy of Sciences, 2011)Many first-line cancer drugs are natural products or are derived from them by chemical modification. The trioxacarcins are an emerging class of molecules of microbial origin with potent antiproliferative effects, which may ...