Kwon, Ohyun

Organic

Biography

Ohyun Kwon received her B.S. (1991) and M.S. (1993) from Seoul National University in South Korea. In 1993, she came to the U.S. to pursue her Ph.D. (1998) from Columbia University under the guidance of S. J. Danishefsky. Her thesis work involved the synthesis of biologically significant glycolipid, asialo GM1 and Globo-H human breast tumor antigen molecule, as well as complex phomoidride terpenoids, CP-225,917 and CP-263,114. She then went to Harvard University as a Howard Hughes Postdoctoral Fellow to study chemical genetics in S. L. Schreiber’s lab. There, she completed a diversity-oriented combinatorial synthesis (DOS) of a library of muticyclic compounds, as well as a library of macrocycles. Kwon joined the faculty as an assistant professor at UCLA in 2001. She has been a member of the Molecular Biology Institute (MBI) and UCLA Jonsson Comprehensive Cancer Center (JCCC) since 2005. 

Research Interests

At the core of the Kwon group’s research lies the design and development of new reactions and reagents that empower the chemical synthesis of natural products and unnatural small molecules of medicinal significance. One of the central themes of the group’s research is the redox-based deconstructive radical chemistry of terpenes, terpenoids, and commodity chemicals, whereas another involves enantioselective phosphorus organocatalysis and the development of novel chiral phosphines such as the HypPhos catalysts now sold by Sigma–Aldrich.

 

Honors & Awards

  • 2019 Novartis Chemistry Lectureship Award
  • 2018 Boehringer Ingelheim Green Chemistry Award
  • 2018 UC CAI Technology Development Award
  • 2008 Glenn T. Seaborg Award
  • 2008 Abbott Lecture, University of Notre Dame
  • 2005 Thieme Journal Award, Synthesis and Synlett
  • 2005 Faculty Career Development Award, UCLA
  • 2004 Faculty Career Development Award, UCLA
  • 2003 Amgen Young Investigator’s Award
  • Columbia University KAST Fellowship

Representative Publications

  • 106.  Swain, M.; Bunnell, T. B.; Kim, J. Kwon, O. “Dealkenylative Alkynylation Using Catalytic Fe(II) and Vitamin C.”  J. Am. Chem. Soc. 2022, doi: https://doi.org/10.1021/jacs.2c05980  [abstract] [pdf]
  • 105.  Hagiwara, H; Watanabe, M.; Fujioka, Y.; Kadosaka, T.; Koizumi, T.; Koya, T.; Nakao, M.; Kamada, R.; Temma, T.; Okada, K.; Moreno, J. M.; Kwon, O.; Sabe, H.; Ohba, Y.; Anzai, T. “Stimulation of the mitochondrial calcium uniporter mitigates chronic heart failure-associated ventricular arrhythmia in mice.” Heart Rhythm 2022, doi: https://doi.org/10.1016/j.hrthm.2022.05.034. [abstract] [pdf]
  • 104.  Khong, S.; Venkatesh, T.; Kwon, O. “Nucleophilic Phosphine Catalysis: The Untold Story” 2021; Asian J. Org. Chem. 2021, http://dx.doi.org/10.1002/ajoc.202100496. [abstract] [pdf]
  • 103.  Shankar, T. S.; Ramadurai, D. K. A.; Steinhorst, K.; Sommakia, S.; Badolia, R.; Krokidi, A. T.; Calder, D.; Navankasattusas, S.; Sander, P.; Kwon, O. S.; Aravamundhan, A.; Ling, J.; Dendorfer, A.; Xie, C.; Kwon, O.; Cheng, E. H. Y.; Whitehead, K. J.; Richardson, R. S.; Spitzer, K. W.; Schdelseker, J.; Chaudhuri, D.; Drakos, S. G. “Cardiac-specific deletion of voltage dependent anion channel 2 leads to dilated cardiomyopathy by altering calcium homeostasis” Nat. Commun. 2021, 12, 4583. [abstract] [pdf]
  • 102.  Xie, C.; Smaligo, A. J.; Song, X.-R.; Kwon, O. “Phosphorus-Based Catalysis” ACS Cent. Sci. 2021, 7,  536–558. [abstract] [pdf]
  • 101. Chen, V. Y.; Kwon, O. “Unified Approach to Furan Natural Products via Phosphine–Palladium Catalysis” Angew. Chem. Int. Ed. 2021, 60, 8874–8881 [abstract] [pdf]
  • 100. Swain, M.; Sadykhov, G.; Wang, R.; Kwon, O. “Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins” Angew. Chem. Int. Ed. 2020, 59, 17565–17571.[abstract] [pdf] Synfacts highlight [Link]
  • 99. Blank, B.; Andrews, I.; Kwon, O. “Phosphine-Catalyzed (4 + 1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines Through Phosphonium Diene Intermediates” ChemCatChem. 2020, 12, 4352–4372. [abstract] [pdf]
  • 98. Wilting, F.; Kopp, R.; Gurnev, P. A.; Schedel, A.; Dupper, N. J.; Kwon, O.; Nicke, A.; Gudermann, T.; Schredelseker, J. “The antiarrhythmic compound efsevin directly modulates voltage-dependent anion channel 2 by binding to its inner wall and enhancing mitochondrial Ca2+ uptake” Br J Pharmacol. 2020, [abstract] [pdf]
  • 97. Smaligo, A. J.; Wu, J.; Burton, N. R.; Hacker, A. S.; Shaikh, A. C.; Quintana, J. C.; Wang, R.; Xie, C.; Kwon, O. “Oxodealkenylative cleavage of alkene C(sp3)–C(sp2) bonds: A practical method for introducing carbonyls into chiral pool materials” Angew. Chem. Int. Ed. 202059, 1211–1215. [abstract] [pdf]
  • 96. Smaligo, A. J.; Kwon, O. “Dealkenylative thiylation of C(sp3)–C(sp2) bonds” Org. Lett. 201921, 8592–8597. [abstract] [pdf]
  • 95. Shaikh, A. C.; Kwon, O. “Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-tosyl-3-pyrroline-3-carboxylate” Org. Synth. 201996, 214–231. [abstract] [pdf]
  • 94. Zhang, K.; Cai, L.; Hong, S.; Kwon, O. “Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones” Org. Lett. 201921, 5143–5146. [abstract] [pdf]
  • 93. Cai, L.; Zhang, K.; Chen, S.; Lepage, R. J.; Houk, K. N.; Krenske, E. H.; Kwon, O. “Catalytic asymmetric Staudinger–aza-Wittig reaction for the synthesis of heterocyclic amines” J. Am. Chem. Soc. 2019141, 9537–9542. [abstract] [pdf]
  • 92. Smaligo, A. J.; Swain, M.; Quintana, J. C.; Tan, M. F.; Kim, D. A.; Kwon, O. “Hydrodealkenylative C(sp3)–C(sp2) bond fragmentation” Science 2019364, 681–685. [abstract] [pdf]
  • 91. Shaikh, A. C.; Kwon, O. “Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate” Org. Synth. 201996, 110–123. [abstract] [pdf]
  • 90. Khong, S.; Xie, C.; Wang, X.; Tan, H.; Kwon, O. “Chiral Aminophosphines Derived from Hydroxyproline and Their Application in Allene–Imine [4 + 2] Annulation” J. Antibiot. 201972, DOI:10.1038/s41429-019-0181-0. [pdf]
  • 89. Liu, H.; Lin, Y.; Zhao, Y.; Xiao, M.; Zhou, L.; Wang, Q.; Zhang, C.; Wang, D.; Kwon, O.; Guo, H. “Phosphine-Promoted [4+3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3+3] and [4+3] Pathways” RSC Adv. 20199, 1214–1221. [abstract] [pdf]
  • 88. Kearney, S. E., et al. “Canvas: a crowd-sourced, natural product screening library for exploring biological space” ACS Central Sci. 2018(12), 1727–1741. [abstract] [pdf]
  • 87. Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. “Phosphine Organocatalysis” Chem. Rev. 2018118 (20), 10049–10293. [abstract] [pdf]
  • 86. Xu, Q.; Dupper, N. J.; Smaligo, A. J.; Fan, Y. C.; Cai, L.; Wang, Z.; Langenbacher, A. D.; Chen, J.; Kwon, O. “Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with α-Methylallenoates” Org. Lett. 201820 (19), 6089–6093. [abstract] [pdf]
  • 85. Lee, C. J.; Swain, M.; Kwon, O. “Synthesis of Cyclic β-Silylalkenyl Triflates via an Alkenyl Cation Intermediate” Org. Lett. 201820 (17), 5474–5477. [abstract] [pdf]
  • 84. Smaligo, A. J.; Vardhineedi, S.; Kwon, O. “Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene–Imine [3 + 2] Annulation” ACS Catal. 2018(6), 5188–5192.  [abstract] [pdf]
  • 83. Zhang, K.; Cai, L.; Yang, Z.; Houk, K. N.; Kwon, O. “Bridged [2.2.1] Bicyclic Phosphine Oxide Facilitates Catalytic γ-umpolung–Wittig Olefination” Chem. Sci. 20189, 1867–1872. [abstract] [pdf]
  • 82. Zhao, J.; Brosmer, J. L.; Tang, Q.; Yang, Z.; Houk, K. N.; Diaconescu, P. L.; Kwon, O. “Intramolecular Crossed [2 + 2] Photocycloaddition by Visible Light-Induced Energy Transfer” J. Am. Chem. Soc. 2017139, 9807–9810. [abstract] [pdf]
  • 81. Schweitzer, M. K.; Wilting, F.; Sedej, S.; Dreizehnter, L.; Dupper, N. J.; Moretti, A.; My, I.; Kwon, O.; Priori, S. G.; Laugwitz, K.-L.; Breit, A.; Schnitzler, M. M.; Gudermann, T.; Schredelseker, J. “Suppression of Arrhythmia by Enhancing Mitochondrial Ca2+ Uptake in Catecholaminergic Ventricular Tachycardia Models” JACC: Basic Translational Science. accepted on 7/3/17. [abstract] [pdf]
  • 80. Fernández-del-Río, L.; Nag, A.; Casado, E. G.; Ariza, J.; Awad, A. M.; Joseph A. I.; Kwon, O.; Verdin, E..; de Cabo, R.; Schneider, C.; Torres, J. Z.; Burón, M. I.; Clarke, C. F.; Villalba, J. M. “Kaempferol increases levels of coenzyme Q in kidney cells and serves as a biosynthetic ring precursor” Free Radical Bio. Med. 2017110, 176–187. [abstract] [pdf]
  • 79. Zhang, K.; Kwon, O. “2-[(4-Methylphenyl)sulfonyl]-5-phenyl-2-aza-5-phosphabicyclo[2.2.1.]heptane” Encyclopedia of reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., 2017, 1–3. DOI: 10.1002/047084289X.rn02004. [abstract] [pdf]
  • 78. Koc, E.; Kwon, O. “Total Syntheses of Heliotridane and Pseudoheliotridane through the 6 Electrocyclization of Nitrodienes” ‘Symposium-in-Print: New Advances in Pericyclic Reactions’ Tetrahedron 201773, 4195–4200. [abstract] [pdf]
  • 77. Fan, Y. C.; Kwon, O. “Beyond MBH” Lewis Base Catalysis, Volume 2 Vedejs E.; Denmark, S. E., Eds.; Wiley-VCH Verlag GmbH & Co, KGaA, Boschstr: Weinheim, Germany, 2016; pp 715–804. [abstract] [pdf]
  • 76. Kibbie, J. J.; Teles, R. M. B.; Wang, Z.; Hong, P.; Montoya, D.; Krutzik, S.; Lee, S.; Kwon, O.; Modlin, R. L.; Cruz, D. “Jagged1 Instructs Macrophage Differentiation in Leprosy” PloS Pathog. 201612, e1005808. [abstract] [pdf]
  • 75. Zhou, Q.-F.; Zhang, K.; Cai, L.; Kwon, O. “Phosphine-Catalyzed Intramolecular Cyclization of α-(β-Nitroethyl)allenoates to Form (Z)-Furanone Oximes” Org. Lett. 201618, 2954–2957. [abstract] [pdf]
  • 74. Cai, L.; Zhang, K.; Kwon, O. “Catalytic Asymmetric Total Synthesis of (–)-Actinophyllic Acid” J. Am. Chem. Soc. 2016138, 3298–3301. [abstract] [pdf]
  • 73. Xiao, Y.; Guo, H.; Kwon, O. “Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Enantioselective Intermolecular Cyclization Reactions” Aldrichimica Acta201649, 3–13. [pdf]
  • 72. Wang; Z.; Xu, X.; Gu, Z.; Feng, W.; Qian, H.; Li, Z.; Kwon, O. “Interrupted Nazarov Cyclization of 1,4-Pentadien-3-ols: Preparation of Cyclopenta[b]indoles” Chem. Commun. 201652, 2811–2814. [abstract] [pdf]
  • 71. Lu, J.; Yoshimura, K.; Goto, K.; Lee, C.; Hamura, K.; Kwon, O.; Tamanoi, F. “Nanoformulation of geranylgeranyltransferase-I inhibitors for cancer therapy: Liposomal encapsulation and pH-dependent delivery to cancer cells” PloS ONE201510, e346b403. [abstract] [pdf]
  • 70. Zhang, K.; Cai, L.; Jiang, X.; Garcia-Garibay, M. A.; Kwon, O. “Phosphine-Mediated Iterative Arene Homologation Using Allenes” J. Am. Chem. Soc. 2015137, 11258–11261. [abstract] [pdf]
  • 69. Fan, Y. C.; Kwon, O. “Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis” Org. Lett. 201517, 2058–2061.[abstract] [pdf]
  • 68. Xie, L. X.; Williams, K.; He, C. H.; Weng, E.; Khong, S.; Rose, T.; Kwon, O.; Bensinger, S.; Marbois, B.; Clarke, C. F. “Resveratrol and para-coumarate serve as ring precursors for coenzyme Q biosynthesis” J. Lipid Res. 201556, 909–919. [abstract] [pdf]
  • 67. Wang, Z.; Kwon, O. “(S)- 4,5-Dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine” Encyclopedia of reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., DOI: 10.1002/047084289X.rn01773 [pdf]
  • 66. Dupper, N. J.; Kwon, O. “Functionalized α,α-Dibromoesters Through Claisen Rearrangements of Dibromoketene Acetals” Org. Lett. 201517, 1054–1057. [abstract] [pdf]
  • 65. Chang, J. W.; Zuhl, A. M.; Speers, A. E.; Niessen, S.; Brown, S. J.; Mulvihill, M. M.; Spicer, T. P.; Southern, M.; Scampavia, L.; Fernandez-Vega, V.; Ferguson, J.; Dix, M. M.; Hodder, P. S.; Rosen, H.; Nomura, D. K.; Kwon, O.; Hsu, K.-L.; Cravatt, B. F. “A selective inhibitor of platelet-activating factor acetylhydrolases 1b2 and 1b3 that impairs cancer cell survival” ACS Chem. Biol. 201510, 925–932. [abstract] [pdf]
  • 64. Zhou, Q.-F.; Zhang, K.; Kwon, O. “Stereoselective Synthesis of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γγ-Umpolung Addition of Sulfonamides to γ-Substituted Allenoates” ‘Symposium-in-Print: Harry Wasserman’ Tetrahedron Lett. 201556, 3273–3276.[abstract] [pdf]
  • 63. Shimizu, H.; Schredelseker, J.; Huang, J.; Lu, K.; Naghdi, S.; Lu, F.; Franklin, S.; Fiji, H. D. G.; Wang, K.; Zhu, H.; Tian, C.; Lin, B.; Nakano, H.; Ehrlich, A.; Nakai, J.; Stieg, A. Z.; Gimzewski, J. K.; Nakano, A.; Goldhaber, J. I.; Vondriska, T. M.; Hajnoczky, G.; Kwon, O.; Chen, J.-N. “Activation of VDAC2 regulates mitochondrial Ca2+ uptake and cardiac rhythmicity” eLife 20154, e04801.[abstract] [pdf]
  • 62. Henry, C. E.; Xu, Q.; Fan, Y. C.; Martin, T. J.; Belding, L.; Dudding, T.; Kwon, O. “Hydroxyproline-derived Pseudo-enantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (-)-Pyrrolines” J. Am. Chem. Soc. 2014136, 11890–11893. [abstract] [pdf]
  • 61. Xiao, Y.; Sun, Z.; Guo, H.; Kwon, O. “Chiral phosphines in nucleophilic organocatalysis” Beilstein J. Org. Chem., Thematic Series on Organo-Phosphorus Chemistry201410, 2089–2121. [abstract] [pdf]
  • 60. Khong, S. N.; Kwon, O. “Phosphine-Initiated General Base-Catalyzed Quinolone Synthesis” Asian J. Org. Chem., Themed Issue on Organocatalysis20143, 453–457. [abstract] [pdf]
  • 59. Wang, Z.; Xu, X.; Kwon, O. “Phosphine Catalysis of Allenes with Electrophiles” Chem. Soc. Rev., Special Issue “Progress in Allene Chemistry” 201443, 2927–2940. [abstract] [pdf]
  • 58. Fan, Y. C.; Kwon, O. “Advances in Nucleophilic Phosphine Catalysis of Alkenes, Allenes, Acetylenes, and MBHADs” Chem. Commun. 201349, 11588–11619. [abstract] [pdf]
  • 57. Zimonjic, D. B.; Chan, L. N.; Tripathi, V.; Lu, J.; Kwon, O.; Popescu, N. C.; Lowy, D. R.; Tamanoi, F. “In vitro and in vivo effects of geranylgeranyltransferase I inhibitor P61A6 on non-small cell lung cancer cells” BMC Cancer201313, 198. DOI:10.1186/1471-2407-13-198. [abstract] [pdf]
  • 56. Creech, G. S.; Kwon, O. “Palladium-catalyzed coupling of electron deficient β-nitrovinyl and o-nitroaryl thioethers for the synthesis of nitrodienes, nitrostyrenes and nitrobiaryls” Chem. Sci. 20134, 2670–2674. [abstract] [pdf]
  • 55. Wang, Z.; Kwon, O. “Phosphine Organocatalysis as a Platform for Diversity-Oriented Synthesis In Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology” Trabocchi, A., Ed.; John Wiley & Sons, Inc., Hoboken, New Jersey, 2013; pp 97-133. [abstract] [pdf]
  • 54. Patel, A.; Barcan, G. A.; Kwon, O.; Houk, K. N. “Origins of 1,6-Stereoinduction in Torquoselective 6π Electrocyclizations”  J. Am. Chem. Soc. 2013, 135, 4878–4883. [abstract] [pdf]
  • 53. Florian, A. E.; Lepensky, C. K.; Kwon, O.; Haynes, M. K.; Sklar, L. A.; Zweifach, A. “Flow Cytometry Enables A High-throughput Homogeneous Fluorescent Antibody-Binding Assay for -Cytotoxic T Cell Lytic Granule Exocytosis” J. Biomol. Screen. 201318, 420–429. [abstract] [pdf]
  • 52. Barcan, G. A.; Patel, A.; Houk, K. N.; Kwon, O. “A Torquoselective 6π Electrocyclization Approach to Reserpine Alkaloids” Org. Lett. 201214, 5388–5391. [abstract] [pdf]
  • 51. Khong, S. N.; Kwon, O. “One-Pot Phosphine-Catalyzed Quinoline Synthesis” J. Org. Chem. 201277, 8257–8267. [abstract] [pdf]
  • 50. Villa, R. A.; Xu, Q.; Kwon, O. “Total Synthesis of (±)-Hirsutine: The Application of Phosphine-Catalyzed [4+2] Annulation of Imine with α-Methyl Allenoate” Org. Lett. 201214, 4634–4637. [abstract] [pdf]
  • 49. Fan, Y. C.; Kwon, O. “Phosphine/Palladium-Catalyzed Syntheses of Alkylidene Phthalans, 3- Deoxyisoochracinic Acid, Isoochracinic Acid, and Isoochracinol” Org. Lett. 201214, 3264–3267. [abstract] [pdf]
  • 48. Andrews, I. P.; Kwon, O. “Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation” Chem. Sci. 20123, 2510–2514. [abstract] [pdf]
  • 47. Khong, S. N.; Kwon, O. “Chiral Aminophosphine Syntheses and Initial Attempts in Enantioselective Double-Michael Indoline Synthesis” Molecules, Special Issue “Asymmetric Catalysis,” 201217, 5626–5650. [pdf]
  • 46. Andrews, I. P.; Blank, B. R.; Kwon, O. “Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3 pyrrolines” Chem. Commun. 201248, 5373–5375. [abstract] [pdf]
  • 45. Jing, C.; Na, R.; Liu, H.; Zhang, L.; Liu, J.; Wang, M.; Zhong, J.; Kwon, O.; Guo, H. “Phosphine-Catalyzed [3+2] and [4+3] Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates” Adv. Syn. Catal. 2012354, 1023–1034. [abstract] [pdf]
  • 44. Xu, Q.; Kwon, O. “Bis(diphenylphsophino)methane” Encyclopedia of reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., DOI: 10.1002/047084289X.rn01439 [e-EROS]
  • 43. Fan, Y. C.; Kwon, O. “Phosphine Catalysis” In Science of Synthesis; List, B., Ed.; Asymmetric Organocatalysis, Vol. 1, Lewis Base and Acid Catalysts; Georg Thieme: Stuttggart, 2012; pp 723-782. [textbook]
  • 42. Chan, L. N.; Watanabe, M.; Kwon, O.; Tamanoi, F. “Small molecule inhibitors of GGTase-I from the heterocycle library derived from phosphine catalysis” In Enzymes; Hrycyna, C.; Bergo, M.; Tamanoi, F., Eds.; Volume 30, Protein Prenylation Part B; Academic Press/Elsevier: Amsterdam, 2011; pp 165-177. [textbook]
  • 41.  Chan, L. N.; Fiji, H. D. G.; Watanabe, M.; Kwon, O.; Tamanoi, F. “Identification and Characterization of Mechanism of Action of P61-E7, a Novel Phosphine Catalysis-Based Inhibitor of Geranylgeranyltransferase-I” PloS ONE20116, e26135. [abstract] [pdf]
  • 40. Szeto, J.; Sriramurthy, V.; Kwon, O. “Phosphine-Initiated General Base Catalysis: Facile Access to Benzannulated 1,3-Diheteroatom Five-Membered Rings via Double-Michael Reactions of Allenes” Org. Lett. 201113, 5420–5423. [abstract] [pdf]
  • 39. Na, R.; Jing, C.; Xu, Q.; Shi, J.; Jiang, H.; Wu, X.; Zhong, J.; Wang, M.; Benitez, D.; Goddard, W. A.; Guo, H.; Kwon, O. “Phosphine-Catalyzed Annulation Reactions of Azomethine Imines: Allene-Dependent [3+2], [3+3], [4+3], and [3+2+3] Pathways” J. Am. Chem. Soc. 2011133, 13337–13348. [abstract] [pdf]
  • 38. Tran, Y. S.; Martin, T. J.; Kwon, O. “Phosphine-Catalyzed [4 + 2] Annulations of 2-Alkylallenoates and Olefins: Synthesis of Multisubstituted Cyclohexenes” Chem. Asian. J. 20116, 2101–2106. [abstract] [pdf]
  • 37. Fan, Y. C.; Kwon, O. “Diversity-Oriented Synthesis Based on the DPPP-Catalyzed Mixed Double-Michael Reactions of Electron-Deficient Acetylenes and β-Amino Alcohols” Molecules, Special Issue “Diversity-Oriented Synthesis” 201116, 3802–3825. [abstract] [pdf]
  • 36. Martin, T. J.; Tran, Y. S; Vakhshori, V. G.; Kwon, O. “Phosphine-Catalyzed β’-Umpolung Addition of Activated α-Alkyl Allenes” Org. Lett. 201113, 2586–2589. [abstract] [pdf]
  • 35. Cruz, D.; Wang, Z.; Kibbie, J.; Modlin, R.; Kwon, O. “Diversity through phosphine catalysis identifies octahydro-1,6-naphthyridin-4-ones as activators of endothelium-driven innate immunity” Proc. Natl. Acad. Sci. U. S. A. 2011108, 6769–6774. [abstract] [pdf]
  • 34. Choi, J.; Mouillesseauex, K.; Wang, Z.; Fiji, H. D. G.; Kinderman, S. S.; Otto, G. W.; Geisler, R.; Kwon, O.; Chen, J.-N. “Aplexone Targets the HMG-CoA Reductase Pathway and Differentially Regulates Arteriovenous Angiogenesis” Development 2011138, 1173–1182. [abstract] [pdf]
  • 33. Andrews, I. P.; Kwon, O. “Phosphine Catalyzed [3+2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate” Org. Synth. 201188, 138–151. [abstract]
  • 32. Wang, Z.; Castellano, S.; Kinderman, S. S.; Argueta, C. E.; Beshir, A. B.; Fenteany, G.; Kwon, O. “Diversity via a Branched Reaction Pathway: Generation of A Library of Sixteen Muticyclic Scaffolds and Identification of Anti-Migratory Agents” Chem. Eur. J. 201117, 649–654. [abstract] [pdf]
  • 31. Creech, G. S.; Kwon, O. “Tandem 6?-Electrocyclization and Cycloaddition of Nitrodienes to Yield Multicyclic Nitroso Acetals” J. Am. Chem. Soc. 2010132, 8876–8877. [abstract] [pdf]
  • 30. Khong, S. N.; Tran, Y. S.; Kwon, O. “Equilibrium Between a Vinylogous Ylide and a Phosphonium Dienolate Zwitterion: Vinylogous Wittig Olefination Versus Vinylogous Aldol-Type Reaction” Tetrahedron 201066, 4760–4768. [abstract] [pdf]
  • 29. Vardhineedi, S.; Kwon, O. “Diphosphine-Catalyzed Mixed Double-Michael Reaction: A Unified Synthesis of Indolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1-oxazines” Org. Lett. 201012, 1084–1087. [abstract] [pdf]
  • 28. Guo, H.; Xu, Q.; Kwon, O. “Phosphine-Promoted [3+3] Annulation of Aziridines with Allenoates: A Facile Entry into Highly Functionalized Tetrahydropyridines” J. Am. Chem. Soc. 2009131, 6318–6319. [abstract] [pdf]
  • 27. Lu, J.; Chan, L.; Fiji, H. D. G.; Dahl, R.; Kwon, O.; Tamanoi, F. “In vivo anticancer effect of a novel inhibitor of protein geranylgeranyltransferase I” Mol. Cancer Ther. 2009, 8, 1218–1226. [abstract] [pdf]
  • 26. Lu, K.; Kwon, O. “Phosphine-catalyzed [4+2] Annulation: Synthesis of Ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate” Org. Synth. 200986, 212–224. [abstract] [pdf]
  • 25. Andrews, I. P.; Kwon, O. “Highly Efficient Palladium-Catalyzed Hydrostannation of Ethyl Ethynyl Ether” Tetrahedron Lett. 200849, 7097–7099. [abstract] [pdf]
  • 24. Creech, G. S.; Zhu, X.; Fonovic, B.; Travis, D.; Kwon, O. “Theory-Guided Design of Bronsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates” Tetrahedron 200864, 6935–6942. [abstract] [pdf]
  • 23. Watanabe, M.; Fiji, H. D. G.; Guo, L.; Chan, L.; Kinderman, S. S.; Slamon, D. J.; Kwon, O.; Tamanoi, F. “Inhibitors of protein geranylgeranyltransferase-I and rab geranylgeranyltransferase identified from a library of allenoate derived compounds” J. Biol. Chem. 2008283, 9571–9579. [abstract] [pdf]
  • 22. Creech, G. S.; Kwon, O. “Alcohol-Assisted Phosphine Catalysis: One-Step Syntheses of Dihydropyrones from Aldehydes and Allenoates” Org. Lett. 200810, 429–432. [abstract] [pdf]
  • 21. Tran, Y. S.; Kwon, O. “Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Cyclohexenes” J. Am. Chem. Soc. 2007129, 12632–12633. [abstract] [pdf]
  • 20. Sriramurthy, V.; Barcan, G. A.; Kwon, O. “Bisphosphine-Catalyzed Mixed Double-Michael Reactions:  Asymmetric Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines” J. Am. Chem. Soc. 2007129, 12928–12929. [abstract] [pdf]
  • 19. Henry, C. E.; Kwon, O. “Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins” Org. Lett. 20079, 3069–3072. [abstract] [pdf]
  • 18. Zhu, X.-F.; Henry, C. E.; Kwon, O. “Stable Tetravalent Phosphonium Enolate Zwitterions” J. Am. Chem. Soc. 2007129, 6722–6723. [abstract] [pdf]
  • 17. Castellano, S.; Fiji, H. D. G.; Kinderman, S. S.; Watanabe, M.; De Leon, P.; Tamanoi, F.; Kwon, O. “Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I” J. Am. Chem. Soc. 2007129, 5843–5845. [abstract] [pdf]
  • 16. Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. “Phosphine Triggered [3+2] Allenoate-Acrylate Annulation: A Mechanistic Enlightenment” Tetrahedron Lett. 200748, 3617–3620. [abstract] [pdf]
  • 15. Dudding, T.; Kwon, O.; Mercier, E. “Theoretical Rationale for Regioselection in Phosphine Catalyzed Allenoate Additions to Acrylates, Imines and Aldehydes” Org. Lett. 20068, 3643–3646. [abstract] [pdf]
  • 14. Tran, Y. S.; Kwon, O. “An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline” Org. Lett. 20057, 4289–4291. [abstract] [pdf]
  • 13. Zhu, X.; Schaffner, A.; Li, R. C.; Kwon, O. “Phosphine-Catalyzed Synthesis of 6-Substituted 2-Pyrones: Manifestation of E/Z-Isomerism in the Zwitterionic Intermediate” Org. Lett. 20057, 2977–2980. [abstract] [pdf]
  • 12. Zhu, X.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. “A Phosphine-Catalyzed Synthesis of 1,3-Dioxan-4-ylidenes” Org. Lett. 20057, 1387–1390. [abstract] [pdf]
  • 11. Zhu, X.; Henry, C. E.; Kwon, O. “A highly diastereoselective synthesis of 3-carbethoxy-2,5-disubstituted-3-pyrrolines by phosphine catalysis” Tetrahedron 200561, 6276–6282. [abstract] [pdf]
  • 10. Du, X.; Chu, H. V.; Kwon, O. “A concise synthesis of the functionalized [5-7-6] tricyclic skeleton of guanacastepene A” Tetrahedron Lett. 200445, 8843–8846. [abstract] [pdf]
  • 9. Du, X.; Chu, H. V.; Kwon, O. “Synthesis of the [5-7-6] Tricyclic Core of Guanacastepene A via an Intramolecular Mukaiyama Aldol Reaction” Org. Lett. 20035, 1923–1926. [abstract] [pdf]
  • 8. Zhu, X.; Lan, J.; Kwon, O. “An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines” J. Am. Chem. Soc. 2003125, 4716–4717. [abstract] [pdf]

Postdoctoral Work

  • 7. Schmidt, D. R.; Kwon, O.; Schreiber, S. L. “Macrolactones in Diversity-Oriented Synthesis: Preparation of a Pilot Library and an Exploration of Factors Controlling Macrocyclization” J. Comb. Chem. 20046, 286–292.  [abstract] [pdf]
  • 6. Kwon, O.; Park, S. B.; Schreiber, S. L. “Skeletal Diversity via a Branched Pathway: Efficient Synthesis of 29,400 Discrete, Polycyclic Compounds and Their Arraying into Stock Solutions” J. Am. Chem. Soc. 2002124, 13402–13404. [abstract] [pdf]

Graduate Work

  • 5. Kwon, O.; Su, D.; Meng, D.; Deng, W.; D. Amico, D. C.; Danishefsky, S. J. “A Stereospecific Geminal Alkylation Scheme En Route To CP-225,917 and CP-263,114” Angew. Chem., Int. Ed. 199837, 1880–1882. [abstract] [pdf]
  • 4. Kwon, O.; Su, D.; Meng, D.; Deng, W.; D?Amico, D. C.; Danishefsky, S. J. “Total Syntheses of CP-225,917 and CP-263,114: Creation of a Matrix Structure By Sequential Aldol Condensation and Intramolecular Heck Ring Closure” Angew. Chem., Int. Ed. 199837, 1877–1880. [abstract] [pdf]
  • 3. Kwon, O.; Danishefsky, S. J. “Synthesis of Asialo GM1. New Insights in the Application of Sulfonamidoglycosidation in Oligosaccharide Assembly: Subtle Proximity Effects in the Stereochemical Governance of Glycosidation” J. Am. Chem. Soc. 1998120, 1588–1599. [abstract] [pdf]
  • 2. Park, T. K.; Kim, I. J.; Hu, S.; Bilodeau, M. T.; Randolf, J. T.; Kwon, O.; Danishefsky, S. J. “Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen” J. Am. Chem. Soc. 1996118, 11488–11500. [abstract] [pdf]
  • 1. Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S.; Yun, J. S. “Oxyanion Orientation in Anionic Oxy-Cope Rearrangement” J. Org. Chem. 199459, 1444–1456. [abstract] [pdf]