CCC & UPCMLD Publications

 

96. Curran, D. P.; Chu, Q.; Yu, M. “CBS reductions with a fluorous prolinol immobilized in a hydrofluoroether solvent.” Org. Lett. 2008, In press.
95.* Mao, S.; Probst, D.; Werner, S.; Chen, J.; Xie, X.; Brummond, K. M.,“A diverging Rh(I)-catalyzed carbocyclization strategy to prepare a library of unique cyclic ethers.” J. Comb. Chem. 2008, In press.
94. Brummond, K. M.; Chen, D.; Painter, T. O.; Mao, S.; Seifried, D. D.,“A Rh(I)-catalyzed cycloisomerization reaction affording cyclic trienones.” Synlett, Special issue on the organic chemistry of allenes and alkynes, 2008, In press.
93. Brummond, K. M.; Yan, B., “Rh(I)-catalyzed cycloisomerization reaction of allenamides: an approach to cyclic enamides.” submitted for publication.
92. Brummond, K. M.; Chen, D., “Mo(CO)6 and [Rh(CO)2Cl]2 catalyzed allenic cyclocarbonylation reactions of alkynones: efficient access to bicyclic dienones.” Org. Lett. 2008, In Press.
91.* Werner, S.; Turner, D. M.; Chambers, P. G.; Brummond, K. M., “Skeletal and appendage diversity as design elements in the synthesis of a discovery library of nonaromatic polycyclic 5-iminooxazolidin-2-ones.” hydantoins, and acylureas.” submitted for publication.
90.* Feng, L.; Du, D.; Fuller, A. A.; Davoren, J. E.; Wipf, P.; Kelly, J. W.; Gruebele, M., “An experimental survey of the transition between two-state and downhill protein folding scenarios.” Proc. Natl. Acad. Sci. USA 2008, in press.
89.* Wright, C. M.; Chovatiya, R. J.; Jameson, N. E.; Turner, D. M.; Zhu, G.; Werner, S.; Huryn, D. M.; Pipas, J. M.; Day, B. W.; Wipf, P.; Brodsky, J. L., “Pyrimidinone-peptoid hybrid molecules with distinct effects on molecular chaperone function and breast cancer cell proliferation.” Bioorg. Med. Chem. 2008, in press.
88.* Brummond, K. M.; Mitasev, B., “Rhodium catalyzed cycloisomerization reactions of allenes in diversity oriented synthesis.” Strategies and tactics in organic synthesis, Honorary Volume for Professor Paul Wender, Volume 7, 2008, 328-366.
87. Xu, X.; Wang, K. Nelson, S. G., “Catalytic asymmetric [4+2] cycloadditions of ketenes and N-thioacyl imines: Alternatives for direct Mannich reactions of enolizable imines.” J. Am. Chem. Soc. 2007, 129, 11690-11691.
86. Wang, K.; Bungard, C. J.; Nelson, S. G., “Stereoselective olefin isomerization leading to asymmetric quaternary carbon construction.” Org. Lett. 2007, 9, 2325-2328.
85.* Huryn, D. M.; Wipf, P., “Natural products as anticancer drugs.” In “Cancer Drug Design and Discovery”; Academic Press, 2007, in press.
84.* Rodina, A.; Vilenchik, M.; Moulick, K.; Aguirre, J.; Kim, J.; Chiang, A.; Litz, J.; Clement, C. C.; Kang, Y.; She, Y.; Wu, N.; Felts, S.; Wipf, P.; Massague, J.; Jiang, X.; Brodsky, J. L.; Krystal, G. W.; Chiosis, G., “Selective compounds define Hsp90 as a major inhibitor of apoptosis in small-cell lung cancer.” Nature Chem. Biol. 2007, 3, 498-507.
83.* Pierce, J. G.; Waller, D. L.; Wipf, P., “Synthesis of functionalized isoindolinones: addition of in situ generated organoalanes to acyliminium ions.” J. Organomet. Chem. (Special on “Insertion Chemistry of the Metal-Carbon Bond” Honoring G. Erker) 2007, 692, 4618-4629.
82. Wipf, P.; Graham, T. H.; Xiao, J., “From natural products to biological tools.” Pure Appl. Chem. 2007, 79(4), 753-761.
81.* Lee, M.; Raguse, T. L.; Schinner, M.; Pomerantz, W. C.; Wang, X.; Wipf, P.; Gellman, S. H., “Origins of the high 14-helix propensity of cyclohexyl-rigidified residues in b-peptides.” Org. Lett. 2007, 9(9), 1801.
80.* Wipf, P.; Gong, H.; Janjic, J. M.; Li, S.; Day, B. W.; Xie, W., “New opportunities for pregnane X receptor (PXR) targeting in drug development. Lessons from enantio- and species-specific PXR ligands identified from a discovery library of amino acid analogues.” Mini-Rev. Med. Chem. 2007, 7(6), 617-625.
79. Waller, D. L.; Stephenson, C. R. J.; Wipf, P., “Spiroketals via oxidative rearrangement of enol ethers.” Org. Biomol. Chem. 2007, 5, 58-60.
78.* Wipf, P.; Werner, S.; Twining, L. A.; Kendall, C., “HPLC determinations of enantiomeric ratios.” Chirality 2007, 19, 5-9.
77. Wan, S.; Green, M. E.; Park, J.-H.; Floreancig, P. E., "Multicomponent approach to the synthesis of oxidized amides through nitrile hydrozirconation." Org. Lett. 2007, 9, 5385-5388.
76. Mitasev, B.; Probst, D.; Brummond, K. M.,“Rhodium catalyzed allenic alder-ene reactions of propioloamides: efficient synthesis of highly unsaturated d-lactams.” Org. Lett. 2007, 347-350.
75.* Lazo, J. S.; Skoko, J. J.; Werner, S.; Mitasev, B.; Bakan, A.; Koizumi, F.; Yellow-Duke, A.; Bahar, I.; Brummond, K. M., “Structurally unique inhibitors of human mitogen-activated protein kinase phosphatase-1 identified in a pyrrole carboxamide library” J. Pharm. Exp. Ther. 2007, 322, 940-947.
74. Brummond, K. M.; Wach, C., “Environmentally benign solvent systems: toward a greener [4 + 2] cycloaddition process.” Mini-Reviews in Organic Chemistry 2007, 4, 89-103.
73. Brummond, K. M.; Deforrest, J. E., “Synthesizing allenes today (1982-2006)” Synthesis, 2007, 6, 795-818.
72.* Kasi, D.; Werner, S.; Brummond, K. M., “Design and synthesis of a 3-pyrroline-2-carboxamide discovery library.” J. Comb. Chem. 2007, 9, 677.
71. Chen, Z.; Weber, S. G., “A high-throughput method for lipophilicity measurement.” Anal. Chem. 2007, 79(3), 1043-1049.
70. del Pozo, C.; Keller, A. I.; Nagashima, T.; Curran, D. P., “Amide bond formation with a new fluorous carbodiimide: Separation by reverse fluorous solid-phase extraction.” Org. Lett. 2007, 9, 4167-4170.
69.* Wang, X.; Nelson, S. G.; Curran, D. P., “The azido acid approach to [b]-peptides: Parallel synthesis of a tri-[b]-peptide library by fluorous tagging.” Tetrahedron 2007, 63, 6141-6145.
68. Chu, Q.; Yu, M. S.; Curran, D. P., “New fluorous/organic biphasic systems achieved by solvent tuning.” Tetrahedron 2007, 63, 9890-9895.
67. Moura-Letts, G.; Curran, D. P., “Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis.” Org. Lett. 2007, 9, 5-8.
66. Mitasev, B.; Yan, B.; Brummond, K. M., “Cycloaddition reactions of amino-acid derived cross-conjugated trienes: stereoselective synthesis of novel heterocyclic scaffolds.” Special Issue Honoring Professor Steven Weinreb, Heterocycles, 2006, 70, 367.
65. Brummond, K. M.; Mitasev, B.,“Synthesis of functionalized D3-pyrrolines via a Ag(I)-catalyzed cyclization of amino-acid derived allenes.” Special Issue honoring Professor Richard F. Heck, Synlett 2006, 3100.
64.* Werner, S.; Iyer, P. S.; Fodor, M. D.; Coleman, C. M.; Twining, L. A.; Mitasev, B.; Brummond, K. M., “Solution-phase synthesis of a tricyclic pyrrole-2-carboxamide discovery library using a Stetter-Paal-Knorr reaction sequence” J. Comb. Chem.  2006, 8, 368.
63. Zhang, W.; Lu, Y.; Chen, C. T.; Curran, D. P.; Geib, S., “Fluorous synthesis of hydantoin-, piperazinedione-, and benzodiazepinedione-fused tricyclic and tetracyclic ring systems.” Eur. J. Org. Chem. 2006, 2055-2059.
62. Matsugi, M.; Yamanaka, K.; Inomata, I.; Takekoshi, N.; Hasegawa, M.; Curran, D. P., “Synthesis of fluorous-Fmoc reagents and purification of protected dipeptides with fluorous solid phase extraction.” Qsar. Comb. Sci. 2006, 25, 713-715.
61. Curran, D. P.; Ogoe, C., “A new fluorous methoxymethyl (FMOM) protecting group for alcohols.” Qsar. Comb. Sci. 2006, 25, 732-735.
60. Curran, D. P.; Bajpai, R.; Sanger, E., “Purification of fluorous Mitsunobu reactions by liquid-liquid extraction.” Adv. Synth. Catal. 2006, 348, 1621-1624.
59. Chu, Q. L.; Zhang, W.; Curran, D. P., “A recyclable fluorous organocatalyst for Diels-Alder reactions.” Tetrahedron Lett. 2006, 47, 9287-9290.
58. Nelson, S. G.; Wang, K., “Asymmetric Claisen rearrangements enabled by catalytic asymmetric di(allyl) ether syntheses.” J. Am. Chem. Soc. 2006, 128, 4232-4233. 
57. Stevens, B. D.; Bungard, C. J.; Nelson, S. G., “Strategies for expanding structural diversity available from olefin isomerization-Claisen rearrangement reactions.” J. Org. Chem. 2006, 71, 6397-6402. 
56.* Shi, G.; Feng, H.; Fang, H.; Liang, Q., Nelson, S. G.; Weber, S. G., “A capillary-based, serial-loading parallel microreactor for catalyst screening.” Anal. Chem. 2006, 78,1972-1979.
55.* Xiao, J.; Weisblum, B.; Wipf, P., “Trisubstituted (E)-alkene dipeptide isosteres as b-turn promoters in the gramicidin S cyclodecapeptide scaffold.” Org. Lett. 2006, 8(21), 4731-4734.
54. Wipf, P.; Pierce, J. G., “Expedient synthesis of the a-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).” Org. Lett. 2006, 8 (15), 3375-3378.
53.* Werner, S.; Turner, D. M.; Lyon, M. A.; Huryn, Donna M.; Wipf, P., “A focused library of tetrahydropyrimidinone amides via a tandem Biginelli-Ugi multi-component process.” Synlett (Special Issue on Cascade Reactions) 2006, (14), 2334-2338.
52. Wipf, P.; Walczak, M. A. A., “Pericyclic cascade reactions of C-bicyclo[1.1.0]butylbenzylamines.” Angew. Chem. Int. Ed. 2006, 45, 4172-4175.
51. Zhang, W.; Curran, D. P., “Synthetic applications of fluorous solid-phase extraction (F-SPE).” Tetrahedron 2006, 62, 11837-11865.
50. Curran, D. P.; Mikami, K.; Soloshonok, V. A., “Current frontiers of fluoroorganic chemistry and recent advances in fluorous chemistry – Preface.” J. Fluorine Chem. 2006, 127, 454-455.
49. Curran, D. P., “Organic synthesis with light-fluorous reagents, reactants, catalysts, and scavengers.” Aldrichim. Acta 2006, 39, 3-9.
48.* Chen, Z.; Yang, Y.; Werner, S.; Wipf, P.; Weber, S. G., “A screening method for chiral selectors that does not require covalent attachment.” J. Am. Chem. Soc. 2006, 128(7), 2208-2209.

47. Brummond, K. M.; Chen, D., “Microwave-assisted intramolecular [2 + 2] allenyne cycloaddition reaction for the rapid and regioselective synthesis of bicyclo[4.2.0]octa-1,6-dienes and bicyclo[5.2.0]nona-1,7-dienes.” Org. Lett. 2005, 7, 3473.
46. Zhao, H.; Wu, L.; Zhang, X.; Crowley, K.; Weber, S. G., “Transport of organic solutes through amorphous teflon AF films.” J. Am. Chem. Soc. 2005, 127, 15112-15119.
45. Yu, M. S.; Curran, D. P.; Nagashima, T., “Increasing fluorous partition coefficients by solvent tuning.” Org. Lett. 2005, 7, 3677-3680.
44. Matsugi, M.; Curran, D. P., “Synthesis, reaction, and recycle of light fluorous Grubbs-Hoveyda catalysts for alkene metathesis.” J. Org. Chem. 2005, 70, 1636-1642.
43. Manku, S.; Curran, D. P., “Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates.” J. Org. Chem. 2005, 70, 4470-4473.
42. Manku, S.; Curran, D. P., “Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes.” J. Comb. Chem. 2005, 7, 63-68.
41. Curran, D. P.; Wang, X. A.; Zhang, Q. S., “Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines.” J. Org. Chem. 2005, 70, 3716-3719.
40. Stevens, B. D.; Nelson, S. G., “Tandem Sakurai-aldol addition reactions as a route to structurally complex carbocycles.” J. Org. Chem. 2005, 70, 4375-4379.
39. Ryu, I.; Matsubara, H.; Emnet, C.; Gladysz, J. A.; Takeuchi, S.; Nakamura, Y.; Curran, D. P., “Fluorous solvents.” In Green Reaction Media in Organic Synthesis; Blackwell: Ames, IO, 2005, p 59-124.
38. Curran, D. P.; Matsugi, M., “Light Fluorous Chemistry.” In: “Fluorous Chemistry”, CMC: Tokyo, 2005, Ch 3, pp 43-66 (in Japanese).
37. Wipf, P.; Xiao, J.; Geib, S. J., “Imine additions of internal alkynes for the synthesis of trisubstituted (E)-alkene and cyclopropane peptide isosteres.” Adv. Synth. Catal. (Special Issue on C-C Bond Formation) 2005, 347, 1605-1613.
36. Wipf, P.; Mahler, S. G.; Okumura, K., “Metathesis reactions of pyrazolotriazinones generate dynamic combinatorial libraries.” Org. Lett. 2005, 7, 4483-4486.
35.* Wipf, P.; Xiao, J.; Jiang, J.; Belikova, N. A.; Tyurin, V. A.; Fink, M. P.; Kagan, V. E., “Mitochondrial targeting of selective electron scavengers: synthesis and biological analysis of hemigramicidin-TEMPO conjugates.” J. Am. Chem. Soc. 2005, 127, 12460-12461.
34. Wipf, P.; Fletcher, J. M.; Scarone, L., “Microwave promoted oxazole synthesis: cyclocondensation cascade of oximes and acyl chlorides.” Tetrahedron Lett. 2005, 46 (33),5463-5466.
33. Werner, S.; Iyer, P. S., “Microwave-assisted synthesis of pyrrole-2-carboxamides.” Synlett 2005, 9, 1405-1408.
32.* Mu, Y.; Stephenson, C. R. J.; Kendall, C.; Saini, S. P. S.; Toma, D.; Ren, S.; Cai, H.; Strom, S. C.; Day, B. W.; Wipf, P.; Xie, W., “A pregnane X receptor agonist with unique species-dependent stereoselectivity and its implications in drug development.” Mol. Pharmacol. 2005, 68, 403-413.
31. Wipf, P.; Xiao, J., “Electrostatic vs steric effects in peptidomimicry.  synthesis and secondary structure analysis of gramicidin S analogs with (E)-alkene peptide isosteres.” J. Am. Chem. Soc. 2005, 127, 5742-5743.
30. Wipf, P.; Stephenson, C. R. J., “Three-component synthesis of a,b-cyclopropyl-g-amino acids.” Org. Lett. 2005, 7, 1137-1140.
29. Wipf, P.; Xiao, J., “Convergent approach to (E)-alkene and cyclopropane peptide isosteres.” Org. Lett. 2005, 7, 103-106.
28.* Janjic, J. M.; Mu, Y.; Kendall, C.; Stephenson, C. R. J.; Balachandran, R.; Raccor, B. S.; Lu, Y.; Zhu, G.; Xie, W.; Wipf, P.; Day, B. W., “New antiestrogens from a library screen of homoallylic amines, allylic amines, and C-cyclopropylalkylamines.” Bioorg. Med. Chem. 2005, 13, 157-164.
27.* Brummond, K. M.; Curran, D. P.; Mitasev, B.; Fischer, S., “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 tricyclic pyrrole library” J. Org. Chem. 2005, 70, 1745-1753.
26. Brummond, K. M.; You, L., “Consecutive Rh(I)-catalyzed Alder-ene/Diels-Alder/Aiels-Alder reaction sequence affording rapid entry to polycyclic compounds.” Invited Tetrahedron Symposia-in-Press Applications in Catalysis in Industry and Academia 2005, 61, 6180.
25. Brummond, K. M.; Chen, D.“Microwave-assisted intramolecular [2 + 2] allenyne cycloaddition reaction for the rapid and regioselective synthesis of bicyclo[4.2.0]octa-1,6-dienes and bicyclo[5.2.0]nona-1,7-dienes.” Org. Lett. 2005, 7, 3473.
24. Brummond, K. M.; Mitasev, B., “Allenes and transition metals: A diverging approach to heterocycles.” Org. Lett. 2004, 6, 2245.
23. Horvath, I. T.; Curran, D. P.; Gladysz, J. A., “Fluorous chemistry: Scope and definition.” In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004, 1-4.
22. Curran, D. P., “Separations with fluorous silica gel and related materials.” In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004, p 101-127.
21. Curran, D. P., “Light fluorous chemistry – a user's guide.” In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004, p 128-156.
20. Ryu, I.; Matsubara, H.; Curran, D. P., “1-Hydroxymethyladamantane. Radical hydroxymethylation with a fluorous tin hydride.” In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004, p 470-471.
19. Ryu, I.; Matsubara, H.; Nakamura, H.; Curran, D. P., “trans-1,2-Dibromocyclohexane. The phase vanishing bromination with FC-72 as a screen phase.” In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004, p 468-470.
18. Curran, D. P.; Dandapani, S., “4-Fluorobenzyl 4-(4-nitrophenyl)butyrate. The Mitsunobu reactions with a fluorous phosphine and a fluorous Dead reagent.” In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004, p 436-437.
17. Dandapani, S.; Curran, D. P., “Separation-friendly Mitsunobu reactions: A microcosm of recent developments in separation strategies.” Chem. Eur. J. 2004, 10, 3130-3138.
16.* Fewell, S. W.; Smith, C. M.; Lyon, M. A.; Dumitrescu, T. P.; Wipf, P.; Day, B. W.; Brodsky, J. L., “Small molecule modulators of endogenous and co-chaperone-stimulated Hsp70 ATPase activity.” J. Biol. Chem. 2004, 279, 51131-51140.
15. Wipf, P.; Janjic, J.; Stephenson, C. R. J., “Microwave-assisted synthesis of allylic amines: considerable rate acceleration in the hydrozirconation-transmetalation-aldimine addition sequence.” Org. Biomol. Chem. 2004, 2, 443-445.
14. Wipf, P.; Coleman, C. M., “Scavenger strategies in organic synthesis – Part II.” Drug Discovery World 2004, Spring issue.
13. Wipf, P.; Coleman, C. M., “Scavenger strategies in organic synthesis – Part I.” Drug Discovery World 2004, Winter issue.
12. Mikami, K.; Matsuzawa, H.; Tekauchi, S.; Nakamura, Y.; Curran, D. P., “b-Cyclodextrin columns for separation of fluorous and non-fluorous compounds: How to use beta-cyclodextrin columns in fluorous mixture synthesis and racemic synthesis.” Synlett 2004, 2713-2716.
11. Matsugi, M.; Curran, D. P., “Reverse fluorous solid-phase extraction: A new technique for rapid separation of fluorous compounds.” Org. Lett. 2004, 6, 2717-2720.
10. Dandapani, S.; Curran, D. P., “Second generation fluorous DEAD reagents have expanded scope in the Mitsunobu reaction and retain convenient separation features.” J. Org. Chem. 2004, 69, 8751-8757.
9. Dandapani, S.; Newsome, J. J.; Curran, D. P., “Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (DadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD).” Tetrahedron Lett. 2004, 45, 6653-6656.
8. Curran, D. P.; Fischer, K.; Moura-Letts, G., “A soluble fluorous palladium complex that promotes heck reactions and can be recovered and reused.” Synlett 2004, 1379-1382.
7. Curran, D. P.; Dandapani, S.; Werner, S.; Matsugi, M., “Fluorous columns are superior to cyclodextrin columns for demixing in fluorous mixture synthesis: When and why to use fluorous silica gel.” Synlett 2004, 1545-1548.
6. Zhang, X.; Zhao, H.; Chen, Z.; Nims, R.; Weber, S. G., “Effect of polymer concentration on partitioning and molecular recognition in plasticized poly(vinyl chloride).” Anal. Chem. 2003, 75, 4257-4264.
5. Werner, S.; Curran, D. P., “Fluorous dienophiles are powerful diene scavengers in Diels-Alder reactions.” Org. Lett. 2003, 5, 3293-3296.
4. Vallin, K. S. A.; Zhang, Q. S.; Larhed, M.; Curran, D. P.; Hallberg, A., “A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation.” J. Org. Chem. 2003, 68, 6639-6645.
3. Nakamura, H.; Usui, T.; Kuroda, H.; Ryu, I.; Matsubara, H.; Yasuda, S.; Curran, D. P., “Fluorous solvent as a new phase-screen medium between reagents and reactants in the bromination and chlorination of alcohols.” Org. Lett. 2003, 5, 1167-1169.
2. Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. Y., “Synthesis and reactions of fluorous carbobenzyloxy (FCBz) derivatives of a-amino acids.” J. Org. Chem. 2003, 68, 4643-4647.
1. Nelson, S. G.; Bungard, C. J.; Wang, K., “Catalyzed olefin isomerization leading to highly stereoselective Claisen rearrangements of aliphatic allyl vinyl ethers.” J. Am. Chem. Soc. 2003, 125, 13000-13001. 

 

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