DENNIS CURRAN

Summary

Affiliation: University of Pittsburgh
Country: USA

Publications

  1. pmc Synthesis of highly enantioenriched 3,4-dihydroquinolin-2-ones by 6-exo-trig radical cyclizations of axially chiral alpha-halo-ortho-alkenyl anilides
    David B Guthrie
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 131:15492-500. 2009
  2. pmc Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents
    Maria Jimenez
    Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260 USA
    Beilstein J Org Chem 7:1372-8. 2011
  3. pmc Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid
    Vladimir Lamm
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 USA
    Beilstein J Org Chem 9:675-80. 2013
  4. pmc CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃
    Julien Monot
    UPMC Univ Paris 06, Institut Parisien de Chimie Moleculaire UMR CNRS 7201, C 229, 4 place Jussieu, 75005 Paris, France
    Beilstein J Org Chem 6:709-12. 2010
  5. pmc Fluorous Chemistry in Pittsburgh: 1996-2008
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA Email
    J Fluor Chem 129:898-902. 2008
  6. ncbi request reprint Radical additions of aryl iodides to arenes are facilitated by oxidative rearomatization with dioxygen
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 128:13706-7. 2006
  7. doi request reprint How do analogous alpha-chloroenamides and alpha-iodoenamides give different product distributions in 5-endo radical cyclizations?
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 130:8437-45. 2008
  8. ncbi request reprint Relative rates and approximate rate constants for inter- and intramolecular hydrogen transfer reactions of polymer-bound radicals
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    J Am Chem Soc 124:14993-5000. 2002
  9. pmc Do alpha-acyloxy and alpha-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals?
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, 219 Parkman Ave, Pittsburgh, PA 15260, USA
    Beilstein J Org Chem 2:10. 2006
  10. doi request reprint Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate
    Andrey Solovyev
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Dalton Trans 42:695-700. 2013

Collaborators

Detail Information

Publications85

  1. pmc Synthesis of highly enantioenriched 3,4-dihydroquinolin-2-ones by 6-exo-trig radical cyclizations of axially chiral alpha-halo-ortho-alkenyl anilides
    David B Guthrie
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 131:15492-500. 2009
    ..These first examples of an approach for axial chiral transfer from a reactive species in the amide to an acceptor suggest broad potential for extension both within and beyond radical reactions...
  2. pmc Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents
    Maria Jimenez
    Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260 USA
    Beilstein J Org Chem 7:1372-8. 2011
    ..A late stage Nozaki-Hiyama-Kishi reaction was then used to form the 22-membered macrolide. The stereoselectivity of this reaction depended on the configurations of the nearby stereocenter at C6...
  3. pmc Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid
    Vladimir Lamm
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 USA
    Beilstein J Org Chem 9:675-80. 2013
    ..Aldehydes can be selectively reduced in the presence of ketones. On a small scale, products are isolated by evaporation of the reaction mixture and direct chromatography...
  4. pmc CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF₃ and BH₃
    Julien Monot
    UPMC Univ Paris 06, Institut Parisien de Chimie Moleculaire UMR CNRS 7201, C 229, 4 place Jussieu, 75005 Paris, France
    Beilstein J Org Chem 6:709-12. 2010
    ..These results set the stage for further studies of the chemistry of CAAC boranes...
  5. pmc Fluorous Chemistry in Pittsburgh: 1996-2008
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA Email
    J Fluor Chem 129:898-902. 2008
    ..A high level, historical overview of work in the fluorous field at the University of Pittsburgh is presented...
  6. ncbi request reprint Radical additions of aryl iodides to arenes are facilitated by oxidative rearomatization with dioxygen
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 128:13706-7. 2006
    ..A chain mechanism involving reaction of the intermediate cyclohexadienyl radical with oxygen to directly generate the aromatized product and the hydroperoxy radical is proposed...
  7. doi request reprint How do analogous alpha-chloroenamides and alpha-iodoenamides give different product distributions in 5-endo radical cyclizations?
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 130:8437-45. 2008
    ..The chlorides and iodides then become complementary precursors, with chlorides giving largely cyclized/reduced products and iodides giving largely cyclized/non-reduced products...
  8. ncbi request reprint Relative rates and approximate rate constants for inter- and intramolecular hydrogen transfer reactions of polymer-bound radicals
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    J Am Chem Soc 124:14993-5000. 2002
    ..Rapid cyclizations of resin-bound aryl radicals will be possible, but slower cyclizations and most bimolecular reactions will be difficult due to the competing polymer/linker hydrogen transfer...
  9. pmc Do alpha-acyloxy and alpha-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals?
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, 219 Parkman Ave, Pittsburgh, PA 15260, USA
    Beilstein J Org Chem 2:10. 2006
    ..Some ketone product is formed in the alpha-acyloxy substrate at low concentrations, but it is unclear whether this product arises through a slow radical fragmentation process or an inefficient, chain-breaking oxidative process...
  10. doi request reprint Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate
    Andrey Solovyev
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Dalton Trans 42:695-700. 2013
    ..The cleavage of ethyl acetate and oxetane is reported as well. A possible mechanism is proposed...
  11. pmc Binary fluorous tagging enables the synthesis and separation of a 16-stereoisomer library of macrosphelides
    Dennis P Curran
    Department of Chemistry, 1101 Chevron Science Center, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, USA
    Nat Chem 4:124-9. 2012
    ..Macrosphelide D was not in this library, and so its assigned structure was incorrect. We determined its constitution by using NMR spectroscopy and its configuration by synthesizing four candidate stereoisomers...
  12. ncbi request reprint The parent borylene: betwixt and between
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 USA
    Angew Chem Int Ed Engl 51:1602-5. 2012
    ..In contrast, reduction of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene dichloroborane and the related dimesityl derivative provide novel CH insertion products that may have arisen from a borylene...
  13. ncbi request reprint Palladium-promoted cascade reactions of isonitriles and 6-iodo-N-propargylpyridones: synthesis of mappicines, camptothecins, and homocamptothecins
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA
    Org Lett 4:3215-8. 2002
    ..Experimental evidence suggests that the process occurs though organopalladium rather than radical intermediates. It is applied to synthesis analogues of mappicine and camptothecin, including the silatecans DB-67 and DB-91 (homo-DB-67)...
  14. ncbi request reprint Total synthesis of a 28-member stereoisomer library of murisolins
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 128:9561-73. 2006
    ..The 16-compound mixture is subjected to hydrogenation, double demixing, and detagging to provide the 16 isomerically pure murisolins. Twelve of these isomers are new, while four match samples from the first library...
  15. ncbi request reprint Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 68:2972-4. 2003
    ..Rate constants for all of these processes are high (>10(8) M(-)(1) s(-)(1)), and the rates are only marginally reduced (<33%) by the introduction of methyl group ortho to the reacting radical...
  16. doi request reprint Synthesis and reactions of N-heterocyclic carbene boranes
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Angew Chem Int Ed Engl 50:10294-317. 2011
    ..This Review provides comprehensive coverage of the synthesis, characterization, and reactions of NHC-boranes...
  17. ncbi request reprint Synthesis and reactions of fluorous carbobenzyloxy (FCbz) derivatives of alpha-amino acids
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    J Org Chem 68:4643-7. 2003
    ..The potential utility of this new family of reagents in both standard fluorous synthesis with spe separation and fluorous quasiracemic synthesis is illustrated with representative reactions of the (F)Cbz-Phe derivatives...
  18. ncbi request reprint Solution-phase mixture synthesis with fluorous tagging en route: total synthesis of an eight-member stereoisomer library of passifloricins
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Angew Chem Int Ed Engl 45:2423-6. 2006
  19. doi request reprint Chemistry. Fluorous tags unstick messy chemical biology problems
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15208, USA
    Science 321:1645-6. 2008
  20. pmc A "shortcut" Mosher ester method to assign configurations of stereocenters in nearly symmetric environments. Fluorous mixture synthesis and structure assignment of petrocortyne A
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 131:5411-3. 2009
    ..These samples and the derived Mosher esters are used to assign the (3S,14S) configuration to petrocortyne A and to validate both the standard and shortcut Mosher methods for use in the petrocortyne family of dialkynyl carbinols...
  21. ncbi request reprint Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis
    Dennis P Curran
    Department of Chemistry and Center for Combinatorial Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 4:2233-5. 2002
    ..Fluorous mixture synthesis is recommended as a new technique to make multiple natural product analogues in a single multistep synthesis...
  22. ncbi request reprint Extractive phase vanishing reactions with dichloromethane, perfluorohexanes, and dibromoethane: slow addition in a test tube
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 6:1021-4. 2004
    ..This mechanism is contrasted with the original diffusive phase-vanishing reactions introduced by Ryu and co-workers...
  23. ncbi request reprint Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 70:3716-9. 2005
    ..A light fluorous phosphine [(p-C(8)F(17)(CH(2))(2)C(6)H(4))PPh(2)] outperforms a commercially available resin-bound phosphine in a competitive benzylation experiment by a factor of about 4...
  24. ncbi request reprint The cascade radical annulation approach to new analogues of camptothecins. Combinatorial synthesis of silatecans and homosilatecans
    D P Curran
    Department of Chemistry and Center for Combinatorial Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Ann N Y Acad Sci 922:112-21. 2000
    ..The parallel synthesis of several libraries of silatecan and homosilatecan libraries is summarized. One of the first-generation silatecans, DB-67, is emerging as a serious candidate for cancer chemotherapy...
  25. ncbi request reprint Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes
    Sukhdev Manku
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Comb Chem 7:63-8. 2005
    ..By comparison, the same library would have required 112 steps if each compound were made individually by parallel synthesis...
  26. ncbi request reprint Second generation fluorous DEAD reagents have expanded scope in the Mitsunobu reaction and retain convenient separation features
    Sivaraman Dandapani
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    J Org Chem 69:8751-7. 2004
    ..The new reagents promise to provide general and complementary solutions for separation problems in Mitsunobu reactions without restricting reaction scope...
  27. ncbi request reprint Ring-closing metathesis approach to dictyostatin
    Cyrous O Kangani
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Org Lett 7:379-82. 2005
    ..The approach provides for facile fragment coupling of two main segments of these natural products at the C10-C11 alkene with high to complete Z-selectivity...
  28. ncbi request reprint On the proof and disproof of natural product stereostructures: characterization and analysis of a twenty-eight member stereoisomer library of murisolins and their Mosher ester derivatives
    Dennis P Curran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 128:9943-56. 2006
    ..The structure of murisolin was proved to be the 4R,15R,16R,19R,20R,34S isomer, whereas the assignment of 16,19-cis-murisolin as RRRSSS was changed to the RSSRRS diastereomer and murisolin A is suggested to be RSRRRS...
  29. ncbi request reprint Cell-based and biochemical structure-activity analyses of analogs of the microtubule stabilizer dictyostatin
    Brianne S Raccor
    Departments of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, USA
    Mol Pharmacol 73:718-26. 2008
    ..The equations accurately predicted biological activity and will help in the design of future analogs...
  30. ncbi request reprint Low-temperature heck reactions of axially chiral o-iodoacrylanilides occur with chirality transfer: implications for catalytic asymmetric heck reactions
    Andre J B Lapierre
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 129:494-5. 2007
  31. ncbi request reprint Simplified discodermolide analogues: synthesis and biological evaluation of 4-epi-7-dehydroxy-14,16-didemethyl-(+)-discodermolides as microtubule-stabilizing agents
    Nakyen Choy
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Med Chem 46:2846-64. 2003
    ..Other variations in the right and left sides of the discodermolide scaffold revealed additional structure/activity information...
  32. ncbi request reprint Heterocyclic alpha-alkylidene cyclopentenones obtained via a Pauson-Khand reaction of amino acid derived allenynes. A scope and limitation study directed toward the preparation of a tricyclic pyrrole library
    Kay M Brummond
    University of Pittsburgh, Department of Chemistry, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 70:1745-53. 2005
    ..The observation that the first generation of 2-alkyl-substituted pyrroles was unstable led to a second generation of 2-carboxamide pyrroles with sufficient stability for biological tests which are in progress...
  33. ncbi request reprint Tubulin assembly, taxoid site binding, and cellular effects of the microtubule-stabilizing agent dictyostatin
    Charitha Madiraju
    Department of Pharmaceutical Sciences, Chemistry, and Pharmacology, University of Pittsburgh, Pittsburgh, Pennsylvania 15261, USA
    Biochemistry 44:15053-63. 2005
    ..These results are consistent with the idea that the macrocyclic structure of dictyostatin represents the template for the bioactive conformation of discodermolide...
  34. ncbi request reprint Separation-friendly Mitsunobu reactions: a microcosm of recent developments in separation strategies
    Sivaraman Dandapani
    Department of Chemistry, University of Pittsburgh, PA 15260, USA
    Chemistry 10:3130-8. 2004
    ..Because so many different strategies have been used, the Mitsunobu reaction is a microcosm for the new field of strategy level separations...
  35. ncbi request reprint Solution-phase mixture synthesis with double-separation tagging: double demixing of a single mixture provides a stereoisomer library of 16 individual murisolins
    Craig S Wilcox
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA, 15260, USA
    Angew Chem Int Ed Engl 44:6938-40. 2005
  36. ncbi request reprint Synthesis and high content cell-based profiling of simplified analogues of the microtubule stabilizer (+)-discodermolide
    Jose M Minguez
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Mol Cancer Ther 1:1305-13. 2002
    ....
  37. ncbi request reprint Solution-phase parallel synthesis with oligoethylene glycol sorting tags. Preparation of all four stereoisomers of the hydroxybutenolide fragment of murisolin and related acetogenins
    Venugopal Gudipati
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 71:3599-607. 2006
    ..The experimental features (reaction, analysis, separation, and characterization) of OEG mixture synthesis are detailed and are compared to and contrasted with those of fluorous mixture synthesis...
  38. ncbi request reprint Discodermolide/Dictyostatin hybrids: synthesis and biological evaluation
    Youseung Shin
    Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA
    Org Lett 4:4443-6. 2002
    ..These are the first macrocyclic analogues of discodermolide and biological activities were evaluated and compared with linear discodermolide analogues...
  39. ncbi request reprint Radical and palladium-catalyzed cyclizations to cyclobutenes: an entry to the BCD ring system of penitrem D
    Alexey Rivkin
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 69:3719-25. 2004
    ..The stereochemical implications of these processes are evaluated, and a Pd-mediated cyclization approach toward the penitrems is also introduced...
  40. ncbi request reprint Resolution of 1-(2-naphthyl)ethanol by a combination of an enzyme-catalyzed kinetic resolution with a fluorous triphasic separative reaction
    Zhiyong Luo
    Fluorous Technologies, Inc, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA
    Org Lett 4:2585-7. 2002
    ..The mixture was subjected to a fluorous triphasic reaction to give both enantiomers of 1-(2-naphthyl)ethanol 2 in high ee without chromatographic separation or fluorous-organic liquid-liquid extractive purification...
  41. doi request reprint Estimated rate constants for hydrogen abstraction from N-heterocyclic carbene-borane complexes by an alkyl radical
    Andrey Solovyev
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 12:2998-3001. 2010
    ..Two promising new reagents with small N-substituents (R = Me) have been identified...
  42. ncbi request reprint Synthesis and biological assays of E-ring analogs of camptothecin and homocamptothecin
    Raghuram S Tangirala
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Bioorg Med Chem 14:6202-12. 2006
    ..The results provide insights into the structural features of the camptothecin E-ring that affect biological activity...
  43. pmc Fluorous parallel synthesis of a piperazinedione-fused tricyclic compound library
    Stefan Werner
    Center for Chemical Methodologies and Library Development UPCMLD, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Comb Chem 11:452-9. 2009
    ..During the method development, a small library containing sixteen analogs was prepared. The optimized conditions were applied to the synthesis of a production library containing ninety analogs...
  44. doi request reprint Second-generation tags for fluorous chemistry exemplified with a new fluorous Mitsunobu reagent
    Qianli Chu
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Org Lett 10:2453-6. 2008
    ....
  45. pmc Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis
    Gustavo Moura-Letts
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 9:5-8. 2007
    ..The transformation is featured in a rapid synthesis of the bottom fragments of the potent anticancer agents (-)-dictyostatin and 6-epi-dictyostatin...
  46. ncbi request reprint Synthesis and biological assessment of simplified analogues of the potent microtubule stabilizer (+)-discodermolide
    Jose M Minguez
    Department of Chemistry, Chevron Science Center, 219 Parkman Avenue, Pittsburgh, PA 15260, USA
    Bioorg Med Chem 11:3335-57. 2003
    ..The results show that even significant structural simplification can lead to analogues with actions related to microtubule targeting...
  47. doi request reprint Asymmetric radical and anionic cyclizations of axially chiral carbamates
    David B Guthrie
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 11:249-51. 2009
    ..The carbamate groups of the products are readily removed...
  48. ncbi request reprint Total and semisynthesis and in vitro studies of both enantiomers of 20-fluorocamptothecin
    Raghuram S Tangirala
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Bioorg Med Chem Lett 15:4736-40. 2005
    ..The lactone ring of 20-fluorocamptothecin hydrolyzes more rapidly than that of camptothecin in PBS. The results provide insight into the role of the 20-hydroxy group in the binding of camptothecin to topoisomerase-I and DNA...
  49. ncbi request reprint Increasing fluorous partition coefficients by solvent tuning
    Marvin S Yu
    Fluorous Technologies, Inc, 970 William Pitt Way, Pittsburgh, PA 15238, USA
    Org Lett 7:3677-80. 2005
    ..These findings suggest an expanded scope for liquid-based separations in fluorous biphasic catalysis, fluorous-tagged reagents, fluorous-supported oligomer synthesis, and related areas. [reaction: see text]..
  50. ncbi request reprint Fluorous dienophiles are powerful diene scavengers in Diels-Alder reactions
    Stefan Werner
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 5:3293-6. 2003
    ..The resulting fluorous derivatives are separated by solid-phase extraction on fluorous silica gel (FSPE). The fluorous [1,2,4]triazoline-3,5-dione 10 reacted with most dienes within seconds or minutes...
  51. ncbi request reprint Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates
    Sukhdev Manku
    Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, USA
    J Org Chem 70:4470-3. 2005
    ..The tagged amino acids were converted to regiosiomeric mixtures of tricyclic hydantoins. Despite the lack of selectivity, the mixtures were demixed and detagged to give 11 individual pure products in just 25 steps...
  52. pmc Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers
    Bin Sui
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 75:2942-54. 2010
    ....
  53. ncbi request reprint Quasiracemic synthesis: concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine
    Qisheng Zhang
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 124:5774-81. 2002
    ..Quasiracemic synthesis is portrayed as the first and simplest of a series of mixture synthesis techniques based on separation tagging, and the prospects for using other types of separation tags are briefly evaluated...
  54. pmc Stereoisomer libraries: total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach
    Sivaraman Dandapani
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Proc Natl Acad Sci U S A 101:12008-12. 2004
    ..This fluorous-tag encoding method is recommended for the efficient synthesis of multiple stereoisomers for spectroscopic studies, biological tests, or other structure-function relationships...
  55. doi request reprint Bond rotation dynamics of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives
    David B Guthrie
    Department of Chemistry, University of Pittsburgh, Pittsburgh Pennsylvania 15260, USA
    J Org Chem 74:4262-6. 2009
    ..The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents...
  56. doi request reprint Aryl-Csp(3) bond rotation barriers of 2-aryl perhydropyrrolo[3,4-c]pyrrole-1,3-diones
    Krishnan Damodaran
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 74:5481-5. 2009
    ..A rationale for the origin of the barriers is presented...
  57. ncbi request reprint Synthesis and evaluation of a novel E-ring modified alpha-hydroxy keto ether analogue of camptothecin
    Wu Du
    University of Pittsburgh, Department of Chemistry, Pittsburgh, PA 15260, USA
    Bioorg Med Chem 10:103-10. 2002
    ..Despite these similarities, the new keto ether analogue is inactive in cell assays, and implications for the structure/activity relationship are discussed...
  58. doi request reprint CBS reductions with a fluorous prolinol immobilized in a hydrofluoroether solvent
    Qianli Chu
    Fluorous Technologies, Inc, UPARC, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA
    Org Lett 10:749-52. 2008
    ..This process is an attractive prototype for the large-scale use, recovery, and reuse of fluorous organocatalysts...
  59. doi request reprint Confirmation of the stereostructure of (+)-cytostatin by fluorous mixture synthesis of four candidate stereoisomers
    Won Hyuk Jung
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Angew Chem Int Ed Engl 47:1130-3. 2008
  60. doi request reprint Radical deoxygenation of xanthates and related functional groups with new minimalist N-heterocyclic carbene boranes
    Shau Hua Ueng
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 12:3002-5. 2010
    ..They exhibit superior performance to first-generation NHC-boranes, providing improved yields in reductions of xanthates and related functional groups...
  61. ncbi request reprint Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis
    Wei Zhang
    Fluorous Technologies, Inc, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA
    J Am Chem Soc 124:10443-50. 2002
    ..Methods for analysis and purification of the intermediates are established for the quality control of the mixture synthesis...
  62. ncbi request reprint Samarium(II) iodide mediated radical/polar crossover reactions of cyclobutenes. An efficient approach to the BCD ring system of the penitrems
    Alexey Rivkin
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 5:419-22. 2003
    ..This reaction shows promise for construction of the BCD ring fragment of the penitrems...
  63. ncbi request reprint Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers
    Fanglong Yang
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    J Am Chem Soc 128:14200-5. 2006
    ..Lagunapyrone was assigned the 6R,7S,19S,20S,21R configuration by comparison of optical rotations...
  64. ncbi request reprint Synthesis, reaction, and recycle of light fluorous Grubbs-Hoveyda catalysts for alkene metathesis
    Masato Matsugi
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 70:1636-42. 2005
    ..The catalysts can be used in a stand alone fashion, or supported on fluorous silica gel...
  65. ncbi request reprint Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers
    Yoshikazu Fukui
    Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA
    Org Lett 8:301-4. 2006
    ..Biological evaluation showed that the monoepimers of the natural product retained highly potent activity...
  66. ncbi request reprint Synthesis and biological evaluation of (-)-16-normethyldictyostatin: a potent analogue of (-)-dictyostatin
    Youseung Shin
    Department of Chemistry, University of Pittsburgh, Pennsylvania 15261, USA
    Org Lett 7:2873-6. 2005
    ..This provides strong evidence that the C16 methyl group of the dictyostatins is oriented toward Phe270 in the paclitaxel-binding site on beta-tubulin...
  67. ncbi request reprint Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin
    Won Hyuk Jung
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15261, USA
    J Med Chem 50:2951-66. 2007
    ..This data and that from previously generated dictyostatin analogs are combined to produce a picture of the structure-activity relationships in this series of anticancer agents...
  68. ncbi request reprint Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas
    Wu Du
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 5:1765-8. 2003
    ..The intermediacy of an alpha-thioalkylamino radical, which is the synthetic equivalent of an imidoyl radical, is invoked...
  69. ncbi request reprint Fluorous mixture synthesis of stereoisomer libraries: total syntheses of (+)-murisolin and fifteen diastereoisomers
    Qisheng Zhang
    Department of Chemistry and Center for Combinatorial Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Am Chem Soc 126:36-7. 2004
    ....
  70. ncbi request reprint Quasienantiomers and quasiracemates: new tools for identification, analysis, separation, and synthesis of enantiomers
    Qisheng Zhang
    Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA
    Chemistry 11:4866-80. 2005
    ..A short history is provided, the terms are defined and illustrated, and recent applications of quasienantiomers, quasiracemates and related species are reviewed...
  71. ncbi request reprint Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones--tools and tactics for solving problems in fluorous mixture synthesis
    Sivaraman Dandapani
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Org Chem 70:9447-62. 2005
    ..This paper presents the details of the FMS of pine sawfly sex pheromones with an emphasis on identification and solving of problems encountered when working with fluorous mixtures...
  72. ncbi request reprint Synthesis and biological evaluation of purealin and analogues as cytoplasmic dynein heavy chain inhibitors
    Guangyu Zhu
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    J Med Chem 49:2063-76. 2006
    ..The inhibitory effect of purealin was concentration dependent and uncompetitive, supporting the hypothesis that it does not compete with the binding of ATP...
  73. doi request reprint Plasma and tissue disposition of non-liposomal DB-67 and liposomal DB-67 in C.B-17 SCID mice
    William C Zamboni
    Department of Pharmaceutical Sciences, School of Pharmacy, University of Pittsburgh, Pittsburgh, PA, 15213, USA
    Invest New Drugs 26:399-406. 2008
    ..We evaluated the tissue and plasma disposition of DB-67 lactone and hydroxy acid after administration of non-liposomal (NL) and liposomal (L) DB-67 in severe combined immunodeficient (SCID) mice...
  74. ncbi request reprint Amide bond formation with a new fluorous carbodiimide: separation by reverse fluorous solid-phase extraction
    Carlos Del Pozo
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 9:4167-70. 2007
    ..The use of HFE-7100 as a fluorous solvent is crucial for the success of the reverse FSPE...
  75. ncbi request reprint Reverse fluorous solid-phase extraction: a new technique for rapid separation of fluorous compounds
    Masato Matsugi
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Org Lett 6:2717-20. 2004
    ..The organic components of the mixture are retained, while the fluorous components pass. [structure: see text]..
  76. doi request reprint Fluorous "racemic" mixture synthesis: polysaccharide-based chiral columns for simultaneous demix and enantioseparation of racemic fluorous tagged compounds
    Takayuki Tonoi
    Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo, Japan
    Chirality 20:597-603. 2008
    ....
  77. ncbi request reprint Systems cell biology knowledge created from high content screening
    Kenneth A Giuliano
    Cellumen, Inc, Pittsburgh, PA 15203, USA
    Assay Drug Dev Technol 3:501-14. 2005
    ..Furthermore, this methodology can also be applied to basic biomedical research on cells...
  78. ncbi request reprint Silatecan DB-67 is a novel DNA topoisomerase I-targeted radiation sensitizer
    Allan Y Chen
    Department of Radiation Oncology, University of California Davis Medical Center, Sacramento, CA 95817, USA
    Mol Cancer Ther 4:317-24. 2005
    ..Together, our data show that DB-67 exhibits potent cytotoxicity and radiosensitization activity by targeting TOP1 in mammalian cells and has great potential for being developed to treat human cancers...
  79. ncbi request reprint Radical cyclization approach to spirocyclohexadienones
    Felix González López de Turiso
    Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
    Org Lett 7:151-4. 2005
    ..This versatile reaction is applied to formal syntheses of the vasopressin inhibitor SR121463A and aza-galanthamine...
  80. ncbi request reprint Analysis of human topoisomerase I inhibition and interaction with the cleavage site +1 deoxyguanosine, via in vitro experiments and molecular modeling studies
    Gary S Laco
    Laboratory of Molecular Pharmacology, Division of Basic Sciences, National Cancer Institute, National Institutes of Health, Bethesda, MD, 20892, USA
    Bioorg Med Chem 12:5225-35. 2004
    ..These results allow for the rational design of more potent Top1 inhibitors through engineered interactions with as yet unutilized Top1 active-site residues including: Glu356, Asn430, and Lys751...
  81. ncbi request reprint Total synthesis of (-)-dictyostatin: confirmation of relative and absolute configurations
    Youseung Shin
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Angew Chem Int Ed Engl 43:4634-7. 2004
  82. ncbi request reprint Synergistic effects of peloruside A and laulimalide with taxoid site drugs, but not with each other, on tubulin assembly
    Ernest Hamel
    Toxicology and Pharmacology Branch, Developmental Threapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute at Frederick, MD 21702, USA
    Mol Pharmacol 70:1555-64. 2006
    ....
  83. ncbi request reprint Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals
    Wu Du
    Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    Bioorg Med Chem 11:451-8. 2003
    ..The silyl radical addition is featured in short semi-syntheses of DB-67 (7-tert-butyldimethylsilyl-10-hydroxy camptothecin) from both camptothecin and 10-hydroxycamptothecin...
  84. ncbi request reprint Phase-vanishing reactions that use fluorous media as a phase screen. Facile, controlled bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide
    Ilhyong Ryu
    Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599 8531, Japan
    J Am Chem Soc 124:12946-7. 2002
    ....
  85. ncbi request reprint A versatile prodrug approach for liposomal core-loading of water-insoluble camptothecin anticancer drugs
    Xinli Liu
    Department of Chemistry and Pharmaceutical Sciences, Markey Cancer Center, University of Kentucky, Lexington, KY 40506, USA
    J Am Chem Soc 124:7650-1. 2002
    ..The rate of formation of the active agent at the tumor site can be controlled through the selection of n (the length of the alkyl spacer group)...