R S Coleman

Summary

Affiliation: The Ohio State University
Country: USA

Publications

  1. doi request reprint A direct and efficient total synthesis of the tubulin-binding agents ceratamine A and B; use of IBX for a remarkable heterocycle dehydrogenation
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 11:2133-6. 2009
  2. ncbi request reprint Total synthesis of eupomatilones 4 and 6: structurally rearranged and atropisomerically fluxional lignan natural products
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 6:4025-8. 2004
  3. ncbi request reprint Asymmetric synthesis of the dibenzocyclooctadiene lignans interiotherin a and gomisin R
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 7:1849-52. 2005
  4. ncbi request reprint Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 7:2289-91. 2005
  5. ncbi request reprint Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products
    Robert S Coleman
    Department of Chemistry, The Ohio State University, Columbus, 43210, USA
    J Org Chem 70:8932-41. 2005
  6. ncbi request reprint Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210 1185, USA
    J Am Chem Soc 127:16038-9. 2005
  7. ncbi request reprint Total synthesis of gymnoconjugatins A and B
    Robert S Coleman
    Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA
    J Org Chem 71:9841-4. 2006
  8. ncbi request reprint Total synthesis of 2'-O-methylmyxalamide D and (6E)-2'-O-methylmyxalamide D
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210 1185, USA
    J Am Chem Soc 129:3826-7. 2007
  9. ncbi request reprint Dependence of DNA sequence selectivity and cell cytotoxicity on azinomycin A and B epoxyamide stereochemistry
    Robert S Coleman
    Department of Chemistry, The Ohio State University, Columbus, OH 43210, USA
    Org Lett 9:1891-4. 2007
  10. ncbi request reprint Synthesis of functional "top-half" partial structures of azinomycin a and B
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    J Org Chem 72:7726-35. 2007

Research Grants

Collaborators

  • Wei Chen
  • R Garg
  • S Alcaro
  • ROBERT BRUEGGEMEIER
  • Mark Berg
  • D M Wilson
  • François Xavier Felpin
  • Catherine J Murphy
  • Sobhan Sen
  • Daniele Andreatta
  • Latha A Gearheart
  • Mark M Somoza
  • Soumya Mitra
  • Gilbert T Kelly
  • Nikolaus P Ernsting
  • Sergey A Kovalenko
  • Eric B Brauns
  • R M Pires
  • Srinivas Reddy Gurrala
  • J Luis Pérez Lustres
  • Roger Smith
  • Coran M H Watanabe
  • Chaomin Liu
  • Hai Liu
  • Evan Rivers
  • J Louis Pérez Lustres
  • Ellen E Connor
  • Nicole A Paraggio
  • Ala Issa
  • Michael D Wyatt
  • W Evan Rivers
  • Mihaela L Madaras

Detail Information

Publications31

  1. doi request reprint A direct and efficient total synthesis of the tubulin-binding agents ceratamine A and B; use of IBX for a remarkable heterocycle dehydrogenation
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 11:2133-6. 2009
    ..Final dehydrogenation proved remarkably facile using IBX...
  2. ncbi request reprint Total synthesis of eupomatilones 4 and 6: structurally rearranged and atropisomerically fluxional lignan natural products
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 6:4025-8. 2004
    ..The structure of eupomatilone 6 is revised...
  3. ncbi request reprint Asymmetric synthesis of the dibenzocyclooctadiene lignans interiotherin a and gomisin R
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 7:1849-52. 2005
    ....
  4. ncbi request reprint Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 7:2289-91. 2005
    ....
  5. ncbi request reprint Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products
    Robert S Coleman
    Department of Chemistry, The Ohio State University, Columbus, 43210, USA
    J Org Chem 70:8932-41. 2005
    ..The syntheses were achieved in six to eight steps from simple aromatic precursors...
  6. ncbi request reprint Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210 1185, USA
    J Am Chem Soc 127:16038-9. 2005
    ..Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps...
  7. ncbi request reprint Total synthesis of gymnoconjugatins A and B
    Robert S Coleman
    Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA
    J Org Chem 71:9841-4. 2006
    ..Convergent and efficient syntheses of the microbial natural products gymnoconjugatin A and B are reported and were based on a linchpin coupling strategy using a boron/tin hetero-bis-metallated butadiene system...
  8. ncbi request reprint Total synthesis of 2'-O-methylmyxalamide D and (6E)-2'-O-methylmyxalamide D
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210 1185, USA
    J Am Chem Soc 129:3826-7. 2007
  9. ncbi request reprint Dependence of DNA sequence selectivity and cell cytotoxicity on azinomycin A and B epoxyamide stereochemistry
    Robert S Coleman
    Department of Chemistry, The Ohio State University, Columbus, OH 43210, USA
    Org Lett 9:1891-4. 2007
    ..Both species were found to have unique selectivity profiles and alkylate DNA in a manner distinct from azinomycin B. Computational docking experiments support altered binding modes for the enantiomers...
  10. ncbi request reprint Synthesis of functional "top-half" partial structures of azinomycin a and B
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    J Org Chem 72:7726-35. 2007
    ..The design and synthesis of a detailed series of functional "top-half" substructures of azinomycin A and B is described...
  11. ncbi request reprint Mitomycin synthetic studies: stereocontrolled and convergent synthesis of a fully elaborated aziridinomitosane
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    J Org Chem 69:7309-16. 2004
    ....
  12. ncbi request reprint Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 6:577-80. 2004
    ....
  13. ncbi request reprint A convergent approach to the mitomycin ring system
    R S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210 1185, USA
    Org Lett 3:1141-4. 2001
    ....
  14. ncbi request reprint Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: organometallic coupling versus standard macrolactonization
    R S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 3:3487-90. 2001
    ..A comparison of the effectiveness of this protocol is made with standard macrolactonization...
  15. ncbi request reprint Studies on the mechanism of action of azinomycin B: definition of regioselectivity and sequence selectivity of DNA cross-link formation and clarification of the role of the naphthoate
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210 1185, USA
    J Am Chem Soc 124:13008-17. 2002
    ..A kinetic assay for agent regioselectivity was used to determine the orientation of binding and covalent cross-link formation...
  16. ncbi request reprint Total synthesis of natural product DNA cross-linking agents
    R S Coleman
    Department of Chemistry, Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA
    Curr Opin Drug Discov Devel 4:435-49. 2001
    ..This review describes recent progress on the total synthesis of four natural product families, including the mitomycins, the structurally and functionally related agent FR-900482, the bis-pyrrole isochrysohermidine and the azinomycins...
  17. ncbi request reprint Role of the azinomycin naphthoate and central amide in sequence-dependent DNA alkylation and cytotoxicity of epoxide-bearing substructures
    Robert S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA
    Org Lett 4:3545-8. 2002
    ..g., 2). Compounds were evaluated for cytotoxicity against two breast cancer cell lines. [structure: see text]..
  18. pmc Covalent cross-linking of duplex DNA using 4-thio-2'-deoxyuridine as a readily modifiable platform for introduction of reactive functionality into oligonucleotides
    R S Coleman
    Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210 1185, USA
    Nucleic Acids Res 25:4771-7. 1997
    ..The sequence selectivity of cross-link formation as a function of tether topology and rigidity was examined, and the thermal stability of the modified duplexes was measured by UV melting experiments...
  19. ncbi request reprint Cellular effects induced by the antitumor agent azinomycin B
    Gilbert T Kelly
    Department of Chemistry, Texas A and M University, College Station, Texas 77843, USA
    Chem Biol 13:485-92. 2006
    ..RT-PCR analysis validated the gene changes, and flow cytometry of azinomycin-treated yeast cells demonstrated a phenotypic S phase shift consistent with transcriptional effects...
  20. ncbi request reprint Total synthesis of the eupomatilones
    Soumya Mitra
    Department of Chemistry, The Ohio State University, Columbus, OH 43210, USA
    J Org Chem 72:8724-36. 2007
    ..Full details of the total syntheses of five members of the eupomatilone family of lignans are reported...
  21. ncbi request reprint Use of electrophilic substitution to form site-specific cross-links in DNA
    R M Pires
    The Ohio State University, Columbus, Ohio, USA
    Curr Protoc Nucleic Acid Chem . 2001
    ....
  22. ncbi request reprint DNA cross-linking by azinomycin B: Monte Carlo simulations in the evaluation of sequence selectivity
    Stefano Alcaro
    Dipartimento di Scienze Farmaco Biologiche, Università di Catanzaro Magna Graecia, 88021 Roccelletta di Borgia, Catanzaro, Italy
    J Med Chem 45:861-70. 2002
    ..Synthetic work on the azinomycins and the information coming from this computational study will be important for the design of more potent or DNA sequence-selective agents based on the azinomycin skeleton...
  23. ncbi request reprint Molecular modeling of DNA cross-linking analogues based on the azinomycin scaffold
    Stefano Alcaro
    Dipartimento di Scienze Farmacobiologiche, Universita Magna Graecia di Catanzaro, I 88021 Roccelletta di Borgia, Catanzaro, Italy
    J Chem Inf Model 45:602-9. 2005
    ..As a result, some interesting SAR considerations have been highlighted and a cross-linking conformation different from that of the azinomycin was identified in a less potent, simplified analogue...
  24. ncbi request reprint Complex local dynamics in DNA on the picosecond and nanosecond time scales
    Eric B Brauns
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA
    Phys Rev Lett 88:158101. 2002
    ..Sequence dependence of the localized dynamics of DNA does not appear within this time range. We infer that 30%-50% of the relaxation is faster than 40 ps, has a nonlogarithmic decay and has a sequence dependent amplitude...
  25. doi request reprint Nanoscale structure and dynamics of DNA
    Mark A Berg
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA
    Phys Chem Chem Phys 10:1229-42. 2008
    ....
  26. ncbi request reprint Sodium-ion binding to DNA: detection by ultrafast time-resolved stokes-shift spectroscopy
    Latha A Gearheart
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA
    J Am Chem Soc 125:11812-3. 2003
    ..Our interpretation is that a subpopulation of helices have sodium cations bound in a fashion that slows the normal dynamics...
  27. ncbi request reprint Power-law solvation dynamics in DNA over six decades in time
    Daniele Andreatta
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, 29208, USA
    J Am Chem Soc 127:7270-1. 2005
    ..The various subcomponents may be so strongly coupled that their motions cannot be treated separately...
  28. ncbi request reprint Role of monovalent counterions in the ultrafast dynamics of DNA
    Sobhan Sen
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA
    J Phys Chem B 110:13248-55. 2006
    ..The lack of change in the spectral shape of the emission shows that neither the broadly distributed power-law relaxation nor the extra nanosecond dynamics are due to heterogeneity in the relaxation rates of different helices...
  29. pmc Effect of protein binding on ultrafast DNA dynamics: characterization of a DNA:APE1 complex
    Sobhan Sen
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA
    Biophys J 89:4129-38. 2005
    ..Stokes-shift measurements of the complex show surprisingly little change in the dynamics within the 40 ps-40 ns time range...
  30. pmc Ultrafast dynamics in DNA: "fraying" at the end of the helix
    Daniele Andreatta
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA
    J Am Chem Soc 128:6885-92. 2006
    ..In addition, a new relaxation with a well-defined relaxation time of 5 ps appears. This process is assigned to the rapid component of "fraying" at the end of the helix...
  31. pmc Effect of lesions on the dynamics of DNA on the picosecond and nanosecond timescales using a polarity sensitive probe
    Mark M Somoza
    Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA
    Nucleic Acids Res 32:2494-507. 2004
    ....

Research Grants18

  1. Asymmetric Synthesis of Cytotoxic Natural Products
    Robert Coleman; Fiscal Year: 2005
    ..abstract_text> ..
  2. AZINOMYCINS--TOTAL SYNTHESIS AND MECHANISM OF ACTION
    Robert Coleman; Fiscal Year: 2001
    ....
  3. Azinomycins - Total Synthesis and Mechanism of Action
    Robert Coleman; Fiscal Year: 2007
    ..abstract_text> ..