Kwon, Ohyun


WebsiteHome URL
Division
Organic
Title
Faculty
Professor
Specialties
Organic
Chemical Biology
Synthesis

Contact Information

Email
Office
Molecular Sciences Building 3505C
(310) 267-4954
Lab
Molecular Sciences Building 3235
(310) 206-9648

Short Biography

Professor Kwon received her B.S. degree in 1991 at Seoul National University in Korea, and her PhD in 1998 from Columbia University. After the postdoctoral stint at Harvard University, she joined the faculty at UCLA in 2001.

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

Our group research interest lies in the area of development of new methodologies for organic transformations, asymmetric organocatalysis, chiral catalyst design, target-oriented synthesis (TOS) of biologically important natural compounds, and diversity-oriented synthesis (DOS) of natural product-like molecules. Methodologies developed and molecules thus built are employed in the investigation of biologically significant processes. Our current research areas are described below.

Dealkenylative Functionalizations of Alkene C(sp3)-C(sp2) Bonds

A recent focus in our laboratory is the activation of alkene C(sp3)–C(sp2) bonds commonly found in abundant plant-based terpene and terpene-derived natural products. These efforts have been shown to have applications in total synthesis and the rapid generation of biologically relevant molecules. Future efforts include developing novel variations of this methodology, as well as designing sustainable catalytic systems for these types of transformations.

Science 2019364, 681–685. [pdf]

Org. Lett. 201921, 8592–8597. [pdf]

Angew. Chem., Int. Ed. 202059, 1211–1215. [pdf]

Phosphine Catalysis

Catalysis facilitated by simple organic molecules (vs. transition metal catalyzed reactions) has recently garnered much attention from many research laboratories in academia and in industry. Our contribution to this exciting field of organocatalysis is the development of organic phosphine catalysis. The phosphine catalyses that we developed are operationally simple: they only require a catalytic amount of a phosphine as a reagent. Therefore, after the reaction, simple evaporation of the reaction solvent and flash column chromatography of the crude reaction mixture provides the desired products in pure forms in typically excellent yields. We have developed over two dozen new phosphine-catalyzed reactions to date, some examples of which are illustrated below.

J. Am. Chem. Soc. 2019141, 9537–9542. [pdf]

Chem. Sci. 2018, DOI: 10.1039/C7SC04381C. [pdf]

  

J. Am. Chem. Soc. 2015137, 11258–11261. [pdf]

Target-Oriented Synthesis (TOS) of Natural Products

One of the central themes of research in our laboratories is development of phosphine-catalyzed allenoate annulations and their applications in the chemical synthesis of natural products and their unnatural analogs of medicinal significance. The synthetic targets we choose are highly relevant to human health, specifically the treatment of the common cold, hypertension, amoebic dysentery, malaria, arrhythmia, and cancer. Presented below are some applications of our methodology towards the synthesis of biologically significant natural products

J. Am. Chem. Soc. 2016138, 3298–3301. [pdf]

J. Am. Chem. Soc. 2013135, 4878–4883. [pdf]

Novel Catalyst Design

Most of the chiral phosphines that have been employed for phosphine catalysis were originally developed as ligands for transition metal catalysis. Chiral phosphines play significant roles in asymmetric catalysis. These chiral ligands are typically divided into three design archetypes: (i) phosphines possessing stereogenic phosphorus centers (e.g., DIPAMP), (ii) phosphines having axial chirality (e.g., BINAP), and (iii) phosphines featuring carbon stereocenters (e.g., DuPhos, DIOP). Although phosphines possessing both carbon and phosphorus stereocenters have been particularly useful in asymmetric catalysis, efficient methodologies for the production of specific enantiomers of C-and-P–chirogenic phosphines remain scarce. Following this rationale, our group developed a new family of L-hydroxyproline (Hyp)-derived [2.2.1] bicyclic phosphine catalysts, currently available from Sigma-Aldrich. These catalysts have shown great synthetic utility, as demonstrated in multiple publications (12), and proven the catalytic potential of the rigid [2.2.1] bicyclic framework. We are currently exploring the use of other natural products as a starting point to develop new families of chiral phosphines that are easily tunable and can be used to facilitate a variety of asymmetric processes.

ACS Catal. 20188, 5188–5192. [pdf]

J. Am. Chem. Soc. 2014136, 11890–11893. [pdf]

Diversity-Oriented Synthesis (DOS) and Chemical Biological Applications

Another area of our group research entails diversity-oriented combinatorial synthesis (DOS) of libraries of small organic molecules and their applications in chemical genetics. In the chemical genetics approach small molecules are systematically screened for the desired biological effects. Thus, identified small molecules are used to modulate the cellular functions of their target proteins, thereby elucidating the molecular mechanism of biologically important processes. When the protein of interest is a cause for a human disease, the hit from the screening in biological assays may also find its use in therapeutic remedies. Our collaboration with biologists in our chemical genetic research resulted in the discovery of several enzyme inhibitors, on one of which we have filed a patent for the development of anti-cancer therapeutics. More recently, another small molecule, dubbed "efsevin," has been show to be a potent modulator of cardiac rhythmicity through regulation of mitochondrial Ca2+ uptake via the voltage-dependent anion channel 2 (VDAC2). It also displays prophylactic activity against ventricular tachycardia in a rodent model of a human heart disease.

Br J Pharmacol. 2020; 1–12. [pdf]

JACC: Basic Transl. Sci. 20172, 737747[pdf]

eLife 20154, e04801. [pdf]

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

Publications

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 Chemistry201443, 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]