Selected Recent Publications- David F. Wiemer

  • Relevance of the C-5 Position to Schweinfurthin Induced Cytotoxicity. Topczewski, J. J.; Callahan, M. P.; Kodet, J. G.; Inbarasu, J. D.; Mente, N. R.; Beutler, J. A.; and Wiemer, D. F.  Bioorg. Med. Chem. 2011, 19, 7570–7581.
  • A Novel Bisphosphonate Inhibitor of Squalene Synthase combined with a Statin and Nitrogenous Bisphosphonate in vitro.  Wasko, B. M.; Smits, J. P.; Shull, L. W.; Wiemer, D. F., and Hohl, R. J.  Lipid Research, 2011, 52, 1957–1964.
  • Synthesis and Reactivity of Alkyl-1,1,1-trisphosphonate Esters, Smits, J. P.; Wiemer, D. F. J. Org. Chem. 2011, 76, 8807–8813.
  • Geranylgeranyl diphosphate synthase: emerging therapeutic target. Wiemer, A. J.; Wiemer, D. F.; Hohl, R. J.  Clinical Pharmacology and Therapeutics, 2011, 90 805–812.
  • A direct conversion of benzylic and allylic alcohols to phosphonates.  Barney, R. J.; Richardson, R. M.; Wiemer, D. F. J. Org. Chem. 2011, 76, 2875–2879.
  • First Total Synthesis of (+)-Vedelianin, a Potent Anti-Proliferative Agent.   Topczewski, J. J.; Wiemer, D. F. Tetrahedron Letters, 2011, 52, 1628–1630.
  • Exploration of Cascade Cyclizations Terminated By Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A.  Topczewski, J. J.; Kodet, J. G.; Wiemer, D. F. J. Org. Chem. 2011, 76, 909–919.
  • Biologically active biotin derivatives of schweinfurthin F.  Ulrich, N. C.; Kuder, C. H.; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem. Letters, 2010, 20, 6716–6720.
  • Synthesis and biological evaluation of a series of aromatic bisphosphonates.  Barney, R. J.; Wasko, B. M.; Dudakovic, A.; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem. 2010, 18, 7212–7220.
  • Fluorescent schweinfurthin B and F analogues with anti-proliferative activity.  Topczewski, J. J.; Kuder, C. H.; Neighbors, J. D.; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem. 2010, 18, 6734–6741.
  • Isoprenoid metabolism as a therapeutic target in Gram-negative pathogens, Wiemer, A. J.; Hsiao, C. C.; Wiemer, D. F. Current Topics in Medicinal Chemistry 2010, 10, 1858–1871.
  • Schweinfurthin A Selectively Inhibits Proliferation and Rho Signaling in Glioma and Neurofibromatosis type 1 Tumor Cells in an NF1-GRD Dependent Manner.  Turbyville, T. J.; Gürsel, D.;  Tuskan, R. G.; Walrath, J. C.; Lipshultz, C. A.; Lockett, S.; Wiemer, D. F.; Beutler, J. A.; Reilly, K. M. Mol. Cancer Ther. 2010, 9, 1234–1243.
  • Structural analogues of schweinfurthin F:  Probing the steric, electronic, and hydrophobic properties of the D-ring substructure. Ulrich, N. C.; Kodet, J. G.; Mente, N. R.; Kuder, C. H.; Beutler, J. A.; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem.2010, 18, 1676–1683.
  • A Tandem Cascade Cyclization-Electrophilic Aromatic Substitution:  Application in the Total Synthesis of (+)-Angelichalcone.   Topczewski, J. J.; Callahan, M. P.; Neighbors, J. D.; Wiemer, D. F. J. Am. Chem. Soc.  2009, 131,14630–14631.
  • Total Synthesis of (+)-Schweinfurthins B and E. Topczewski, J. J.; Neighbors, J. D.; Wiemer, D. F. J. Org. Chem. 2009, 74, 6965–6972.
  • Identification of light-independent inhibition of human immunodeficiency virus-1 infection through bioguided fractionation of Hypericum perforatum. Maury, W.; Price, J.; Brindley, M. A.; Oh, C. S.; Neighbors, J. D.; Wiemer, D. F.; Wills, N.; Carpenter, S.; Hauck, C.; Murphy, P.; Widrlechner, M. P.; Delate, K.; Kumar, G.; Kraus, G. A.; Rizshsky, L.; Nikolau, B. Virology Journal, 2009, 6, 101.
  • Synthesis of the cis-fused hexahydroxanthene skeleton  via cationic cascade cyclization.  Neighbors, J. D.; Topczewski, J. J.; Swenson, D. C.; Wiemer, D. F. Tetrahedron Letters, 2009, 50, 3881–3884.
  • Hypericum in Infection: Identification of Anti-viral and Anti-inflammatory Constituents. Birt, D.F.; Widrlechner, M. P.; Hammer, K. D. P.; Hillwig, M. L.; Wei, J.; Kraus, G. A.; Murphy P. A.; McCoy, J.; Wurtele, E. S.; Neighbors, J. D.; Wiemer, D. F.; Maury, W. J.; Price, J. P. Pharmaceutical Biology, 2009, 47, 774-782.
  • Synthesis and biological activity of a fluorescent schweinfurthin analogue. Kuder, C. H.; Neighbors, J. D.; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem. 2009, 17, 4718-4723.
  • The Intermediate Enzymes of Isoprenoid Metabolism as Anticancer Targets.  Wiemer, A. J.; Hohl, R. J.; Wiemer, D. F. Anticancer Agents in Medicinal Chemistry, 2009, 9 526-542 (invited review).
  • A Concise Synthesis of Pawhuskin A. Neighbors, J. D.; Buller, M. J.; Boss, K. D.; Wiemer, D. F. J. Natural Products  2008, 71, 1949-1952.
  • Pseudohypericin is necessary for the light-activated inhibition of Prostaglandin E2 production by Hypericum perforatum.  Hammer, K. D. P.; Hillwig, M. L.; Neighbors, J. D.; Sim, Y. J.; Kohut, M. L.; Wiemer, D. F.; Wurtele, E. S.; Birt, D. F. Phytochemistry, 2008, 69, 2354–2362. 
  • BF3·Et2O Mediated Cascade Cyclizations: Synthesis of Schweinfurthins F and G. Mente, N. R.; Neighbors, J. D.; Wiemer, D. F. J. Org. Chem. 2008, 73, 7963–7970.
  • Pivaloyloxymethyl-modified isoprenoid bisphosphonates display enhanced inhibition of cellular geranylgeranylation. Wiemer, A. J.; Yu, J. S.; Shull, L. W.; Barney, R. J.; Wasko, B. M.; Lamb, K. M; Hohl, R. J.; Wiemer, D. F.  Bioorg. Med. Chem. 2008, 16, 3652–3660.
  • Synthesis of the schweinfurthin hexahydroxanthene core through Shi epoxidation. Neighbors, J. D.; Mente, N. R.; Boss, K. D.; Zehnder, D. W. II; Wiemer, D. F. Tetrahedron Letters, 2008, 49, 516–519.
  • Mono- and Dialkyl Isoprenoid Bisphosphonates as Geranylgeranyl Diphosphate Synthase Inhibitors.  Wiemer, A. J.; Yu, J. S.; Lamb, K. M; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem. 2008, 16, 390–399.
  • Temperature Effects on Stereocontrol in the Horner-Wadsworth-Emmons Condensation with a-Phosphono Lactones.  Yu, J. S.; Wiemer, D. F. J. Org. Chem. 2007, 72, 6263–6265.
  • Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor nutria) by GC-MS and GC-IR.  Lee, H.; Finckbeiner, S.; Yu, J.S.; Wiemer, D. F.; Eisner, T.; Attygalle, A. B. J. Chromatography A  2007, 1165, (1-2), 136-143.
  • Total Synthesis of R,R,R- and S,S,S-Schweinfurthin F: Divergence of Bioactivity in the Enantiomeric Series. Mente, N. R.; Wiemer, A. J.; Neighbors, J. D.; Beutler, J. A.; Hohl, R. J.; Wiemer, D. F. Bioorg Med. Chem. Letters, 2007, 17, 911–915.
  • Synthesis of Fluorescently Tagged Isoprenoid Bisphosphonates that Inhibit Protein Geranylgeranylation. Maalouf, M. A.; Wiemer, A. J.; Kuder, C. H.; Hohl, R. J.; Wiemer, D. F. Bioorg Med. Chem. 2007, 15, 1959–1966.
  • Synthesis and Biological Activity of Isoprenoid Bisphosphonates. Shull, L. W.; Wiemer, A. J.; Hohl, R. J.; Wiemer, D. F. Bioorg. Med. Chem. 2006, 14, 4130–4136.   .
  • The Schweinfurthins: Issues in Development of a Plant-Derived Anticancer Lead. Beutler, J. A.; Jato, J.; Cragg, G.; Wiemer, D. F.; Neighbors, J. D.; Salnikova, M. S.; Hollingshead, M.; Scudiero, D. A.; McCloud, T. G. In: Medicinal and Aromatic Plants, edited by R. J. Bogers, Springer, 2006.
  • Synthesis and Structure-Activity Studies of Schweinfurthin B Analogs:  Evidence for the Importance of a D-Ring Hydrogen Bond Donor in Expression of Differential Cytoxicity. Neighbors, J. D.; Salnikova, M. S.; Beutler, J. A.; Wiemer, D. F. Bioorg. Med. Chem. 2006, 14, 1771–1784.
  • Synthesis of Farnesol Isomers via a Modified Wittig Procedure. Yu, J. S.; Kleckley, T. S.; Wiemer, D. F. Org. Lett. 2005, 7, 4803–4806.
  • Synthesis of Aromatic Phosphates via Cycloaddition of Phosphate Dienes. Kim, M. K.;  Wiemer, D. F. Tetrahedron Letters 2005, 46, 7583–7587.
  • Synthesis of Arieianal, a Prenylated Benzoic Acid from Piper arieianum. Odejinmi, S. I.; Wiemer, D. F. J. Natural Products  2005, 68, 1375–1379.
  • Application of benzyl protecting groups in the synthesis of prenylated aromatic compounds.  Odejinmi, S. I.; Wiemer, D. F. Tetrahedron Letters 2005, 46, 3871–3874.
  • Total synthesis of pawhuskin C: A dianion directed ortho metallation approach. Neighbors, J. D.; Salnikova, M. S.; Wiemer, D. F. Tetrahedron Letters 2005, 46, 1321–1324.
  • Synthesis of Nonracemic 3-Deoxyschweinfurthin B. Neighbors, J. D.; Beutler, J. A.; Wiemer, D. F. J. Org. Chem. 2005, 70, 925–931.
  • Copper-Mediated Displacements of Allylic THP Ethers on a Bisphosphonate Template, Shull, L. W.; Wiemer, D. F. J. Organomet. Chem. 2005, 690, 2521–2530.
  • Synthesis and Activity of Fluorescent Isoprenoid Pyrophosphate Analogues. Kim, M. K.; Kleckley, T. S.; Wiemer, A. J.; Holstein, S. A.; Hohl, R. J.; Wiemer, D. F.J. Org. Chem. 2004, 69, 8186–8193.
  • EDC-Mediated condensations of 1-chloro-5-hydrazino-9,10-anthracenedione,  1-hydrazino-9,10-anthracenedione, and the corresponding anthrapyrazoles.  Kim, M. K.; Wiemer, D. F. Tetrahedron Lett. 2004, 45,4977–4980.
  • α-Phosphono Lactone Analogues of Cytidine and Cytosine Arabinoside Diphosphates: Synthesis via Ring Closing Metathesis.  Chen, X.; Wiemer, D. F.; J. Org. Chem. 2003, 68, 6597–6604.
  • Synthesis of 5’-Amino-5’-Phosphonate Analogs of Pyrimidine Nucleoside Monophosphates. Chen, X.; Wiemer, D. F.; J. Org. Chem. 2003, 68, 6108–6114.
  • Addition of allylindium reagents to acyl phosphonates: Synthesis of tertiary α-hydroxy alkylphosphonates. Kim, D. Y.; Wiemer, D. F. Tetrahedron Lett. 2003, 44, 2803–2805.
  • Tripeptide Probes for Tripeptidyl Protease I Production via Gene Transfer. Kim, M. K.; Mao, Q. W.; Davidson, B. L.; Wiemer, D. F. J. Med. Chem. 2003, 46 1603–1608.
  • Isoprenoid Pyrophosphate Analogues Regulate Expression of Ras-related Proteins, Holstein, S. A.; Wohlford-Lenane, C. L.; Wiemer, D. F.; Hohl, R. J.; Biochemistry 2003, 42, 4384–4391.
  • Tandem Reduction-Reductive Alkylation of Azidosugars. Chen, L.; Wiemer D. F. Tetrahedron Lett. 2002, 43, 2705–2708.
  • Synthesis of Phosphonate Analogs of Cytosine Arabinoside Monophosphate. Chen, X.; Jung, K. Y.; Hohl, R. J.; Wiemer, A. J.; Wiemer, D. F. Phosphorus, Sulfur, Silicon, 2002, 177, 1783 –1786.
  • Synthesis of N-Alkyl α-Phosphonolactams via Enolate Chemistry. Du, Y. M.; Wiemer, D. F. Phosphorus, Sulfur, Silicon, 2002, 177, 2133.
  • α-Phosphono Lactone Analogues of Farnesyl Pyrophosphate: An Asymmetric Synthesis via Ring Closing Metathesis. Du, Y. M.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5701 –5708.
  • Preparation of α-Phosphono Lactams via Electrophilic Phosphorus Reagents: An Application in Synthesis of Lactam-Based Farnesyl Transferase Inhibitors. Du, Y. M.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5709 –5717.
  • Chiral HPLC Separation and Chiroptical Properties of the Enantiomers of Dimethyl α-hydroxyfarnesylphosphonate, a precursor of an FPTase Inhibitor. Caccamese, S.; Du, Y. Wiemer, D. F. J. Chromatography A 2002, 966, 221 –225.
  • Synthesis of a Carbon Analog of N-Acetyl Mannosamine via Acetolysis of a Relatively Stable Ozonide. Chen, L.; Wiemer, D. F. J. Org. Chem. 2002, 67, 7561 –7564.
  • A Cascade Cyclization Approach to Schweinfurthin B. Treadwell, E. M.; Neighbors, J. D.; Wiemer, D. F. Org. Letters 2002, 4, 3639 –3642.
  • A One-Flask Synthesis of α,α-Bisphosphonates via Enolate Chemistry, Du, Y.; Jung, K. Y.; Wiemer, D. F. Tetrahedron Lett. 2002, 43, 8665 –8668.
  • Stereoselective Synthesis of 5’-Hydroxy 5’-Phosphonate Derivatives of Cytidine and Cytosine Arabinoside. Chen, X.; Wiemer, D. F.; Wiemer, A. J.; Hohl, R. J.; J. Org. Chem. 2002, 67, 9331 –9339.
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