California NanoSystems Institute

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Michael Jung, Ph.D.

Director, Bioscience Synthetic Chemistry

Professor, Chemistry and Biochemistry, Organic Chemistry

Member, JCCC Cancer Cell Biology Program Area, JCCC Basic Research, California NanoSystems Institute

Researcher, Chemical Biology, Organic, Synthesis

Education:

Degrees:

Ph.D., Columbia University, 1973
B.A., Rice University, 1969

Honors and Awards:

American Chemical Society , American Chemical Society Arthur C. Cope Scholar Award
Auspex Pharmaceutical Co., Inc., Auspex Horizon Award
Tokushima University, Fujii-Ohtsuka Professor
UCLA, Inaugural UCLA Gold Shield Faculty Prize
UCLA, UCLA Distinguished Teaching Award
UCLA, UCLA Hanson-Dow Teaching Award
UCLA, UCLA McCoy Award
Alfred P. Sloan Fellow
Arthur C. Cope Scholar Award
Camille and Henry Dreyfus Teacher-Scholar
Fulbright-Hays Senior Research Scholar
Glenn T. Seaborg Award

Academic Experience:

Academic Experience:

1973 - 1974 ETH, Zurich, NATO Postdoctoral Fellow

Contact Information:

Email Address:	mej@chem.ucla.edu
Work Email Address:	jung@chem.ucla.edu

Laboratory Address:	Mol Sci Bldg 3210
Work Address:	Mol Sci Bldg 3505A

Home Page:	http://www.chem.ucla.edu/~jung/home.html

Work Phone Number:	1 (310) 825-7954

Research Interests:

The majority of the research personnel in my group are currently engaged in three general fields of interest: the development of new synthetic methods, the total synthesis of biologically active natural products, and medicinal chemistry. We are pursuing the total synthesis of potent antiviral agents, e.g., modified nucleosides and betulinic acid derivatives, several promising antitumor agents, e.g., tedanolide and 13-deoxytedanolide, eleutherobin, dichlorolissoclimide, haterumaimide E, the auripyrones, and laurenediterpenol. The use of epoxide rearrangements in synthesis, e.g., the non-aldol aldol process, and others, is under investigation as well, especially for the synthesis of new antibiotics of the erythromycin class. We are also studying the use of various reactions (e.g., Diels-Alder reactions, bridged Robinson annulation, [3,3] rearrangements) for the synthesis of biologically active molecules, e.g., the acetylcholinesterase inhibitors, the arisugacins; the immunosuppressive agent brasilicardin A; the antibacterial agent mycosporulone; and multiple drug resistance reversing agents such as welwitindolinone C. In particular, we are developing the mixed Lewis acid system, 5-10:1 AlBr3:AlMe3, in a variety of reactions, e.g., cycloadditions, nucleophilic additions, etc. We are developing new processes for the efficient synthesis of various oxygenated steroids, e. g., the cardioactive compound ouabain and the antitumor compound, rhodexin A. We have several collaborative programs in medicinal chemistry, e.g., to prepare various naturally occurring oxidation products of arachidonic acids, the epoxy isoprostanes (which are involved in the onset of atherosclerosis); to develop a new method of delivering antibacterial agents to resistant bacterial strains; the preparation and testing of new selective binders for both the estrogen and the androgen receptors as anti-cancer agents; the synthesis of molecules which differentiate stem cells into osteoblasts; the preparation of molecules to bind to the Sortase-A binding pocket to determine the structure of this important medicinal target; small molecule inhibitors of the growth of various viruses; and agents to stop the growth of tuberculosis.

Additional Information:

Mike Jung received his Bachelor of Arts in 1969 from Rice University, doing research with Richard Turner, and then his PhD in 1973 from Columbia, where he worked with Gilbert Stork. After a one-year NATO postdoctoral fellowship with Albert Eschenmoser at the ETH in Zurich, he joined the faculty at UCLA in 1974. He has risen through the ranks at UCLA and is now a Distinguished Professor of Chemistry. He has served as a reviewer of proposals for various organizations, e.g., NSF, PRF, NIH Medicinal Chemistry Study Section, Research Corporation and others. He is on the Scientific Advisory Boards of several pharmaceutical firms and consults currently for more than 20 industrial laboratories in both the biotech and big pharma settings. Professor Jung is an authority on synthetic organic and medicinal chemistry and has more than 25 patents arising from both his consulting activities and his own research. His current interests include the easy preparation of hindered systems via both Diels-Alder reactions using a new mixed Lewis acid catalyst and via an unusual formal [3,3]-sigmatropic rearrangement. He has also pioneered the use of epoxide rearrangements in synthesis (e.g., the non-aldol aldol) and has investigated new types of gem-disubstituent effects in synthesis. He has published more than 250 articles in refereed journals and has given over 470 lectures on his research, including lectures in German and French. Finally one of his recent compounds is in Phase 1/2a clinical trials for the treatment of hormone refractory prostate cancer.

Selected Publications:

M. E. Jung and S.-J. Min, Synthetic Approaches to the Synthesis of Arisugacin A, Tetrahedron, in press.

J. M. Tsay, M. Trzoss, L. Shi, X. Kong, M. Selke, M. E. Jung, and S. Weiss, Singlet Oxygen Production by Peptide-Coated Quantum Dot-Photosensitizer Conjugates, J. Am. Chem. Soc., in press.

N. Suree, M. E. Jung, and R. T. Clubb, Recent Advances Towards New Anti-infective Agents that Inhibit Cell Surface Protein Anchoring in Staphylococcus aureus and Other Gram-positive Pathogens, Mini Reviews in Medicinal Chemistry, submitted.

M. C. Duncan, D. G. Ho, J. Huang, M. E. Jung, and G. S. Payne, Compound Synthetic Lethal Identification Membrane Traffic Inhibitors, PNAS, in press.

Jung, M. E. Perez, F. , Synthesis of 2-substituted 7-hydroxybenzofuran-4-carboxylates via addition of silyl enol ethers to o-benzoquinone esters, Org Lett, 2009, 11 (10), 2165-7.

Jung, M. E. Allen, D. A. , Use of 4-cyanocoumarins as dienophiles in a facile synthesis of highly substituted dibenzopyranones, Org Lett, 2009, 11 (3), 757-60.

M. E. Jung and D. Ho, Stepwise Acid-Promoted Double-Michael Process: an Alternative to Diels-Alder Cycloadditions for Hindered Silyloxydiene-Dienophile Pairs, Org. Lett., 2007, 9, 375-378.

M. E. Jung and M. Murakami, Total Synthesis of (+/-)-Hedychilactone B: Stepwise Allenoate Diene Cycloaddition to Prepare Trimethyldecalin Systems, Org. Lett., 2007, 9, 461-463.

M. T. Naik, N. Suree, N. U. Ilangovan, C. K. Liew, J. Clemens, M. E. Jung, and R. T. Clubb, A Calcium Modulated Loop Closure Mechanism Activates Cell Surface Protein Anchoring by the Staphylococcus aureus Sortase A Transpeptidase, J. Biol. Chem., 2006, 281, 1817-1826.

M. E. Jung and W.-J. Kim, Practical Syntheses of Dyes for Difference Gel Electrophoresis (DIGE), Bioorg. Med. Chem., 2006, 14, 92-97.

M. E. Jung and B. A. Duclos, Synthetic Approach to Analogues of Betulinic Acid, Tetrahedron, 2006, 62, 9321-9334.

Y.-L. Zhao, C. P. Suhrada, M. E. Jung and K. N. Houk, The 3-Vinylmethylenecyclo-butane-4-Methylenecyclohexene Rearrangement: Theoretical Investigation of a Stereo-selective Stepwise Cope Rearrangement, J. Am. Chem. Soc., 2006, 128, 11106-11113.

M. E. Jung and M. Murakami, Total Synthesis of (+/-)-Hedychenone: Trimethyldecalin Terpenes via Stepwise Allenoate Diene Cycloaddition, Org. Lett., 2006, 8, 5857-59.

Y. Akiba, M. E. Jung, S. Ouk, and J. D. Kaunitz, A Novel Small Molecule CFTR Inhibitor Attenuates HCO3- Secretion And Duodenal Ulcer Formation In Rats, Amer. J. Physiol. GI Liver Physiol., 2005, 289, G753-G759.

M. E. Jung and A. R. Novack, Formation of 3,4-Dimethyl-2-pyrones from Allene Carboxylates and 2-Silyloxydienes via 3-Carboethoxyethylidene Cyclobutanols, Tetrahedron Lett., 2005, 46, 8237-8240.

M. E. Jung and G. Piizzi, Gem-Disubstituent Effect: Theoretical Basis and Synthetic Applications, Chem Rev., 2005, 105, 1735-1766.

M. E. Jung and S.-J. Min, Intramolecular Diels-Alder Reactions of Optically Active Allenic Ketones: Chirality Transfer in the Preparation of Substituted Oxa-bridged Octalones, J. Am. Chem. Soc., 2005, 127, 10834-5.

M. E. Jung, J. J. Clemens, N. Suttee, C. K. Liew, and R. T. Clubb, Synthesis of (2R, 3S) 3-Amino-4-mercapto-2-butanol, a Threonine Analogue for Covalent Inhibition of Sortases, Bioorg. Med. Chem. Letts., 2005, 15, 5076-5079.

Jung, M. E. Clemens, J. J. Suree, N. Liew, C. K. Pilpa, R. Campbell, D. O. Clubb, R. T. , Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases, Bioorg Med Chem Lett, 2005, 15 (22), 5076-9.

Jung, M. E. Ho, D. Chu, H. V. , Synthesis of highly substituted cyclohexenes via mixed Lewis acid-catalyzed Diels-Alder reactions of highly substituted dienes and dienophiles, Org Lett, 2005, 7 (8), 1649-51.

M. E. Jung and A. Maderna, Synthesis of Bicyclo[2.2.2]oct-5-en-2-ones via a Tandem Intermolecular Michael Addition Intramolecular Aldol Process (a Bridged Robinson Annulation), Tetrahedron Lett., 2005, 46, 5057-5061.

M. E. Jung, D. Ho, and H. V. Chu, Synthesis of Highly Substituted Cyclohexenes via Mixed Lewis Acid-Catalyzed Diels-Alder Reactions of Highly Substituted Dienes and Dienophiles, Org. Lett, 2005, 7, 1649-51.

M. E. Jung, J. A. Berliner, D. Angst, D. Yue, L. Koroniak, A. D. Watson, and R. Li, Total Synthesis of the Epoxy Isoprostane Phospholipids PEIPC and PECPC, Org. Lett., 2005, 7, 3933-35.

Jung, M. E. Berliner, J. A. Angst, D. Yue, D. Koroniak, L. Watson, A. D. Li, R. , Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC, Org Lett, 2005, 7 (18), 3933-5.

M. E. Jung, N. Nishimura, and A. R. Novack, Versatile Diastereoselectivity in Formal [3,3]-Sigmatropic Shifts of Substituted 1-Alkenyl-3-alkylidenecyclobutanols and Their Silyl Ethers, J. Am. Chem. Soc., 2005, 127, 11206-7.

Jung, M. E. Nishimura, N. Novack, A. R. , Versatile diastereoselectivity in formal [3,3]-sigmatropic shifts of substituted 1-alkenyl-3-alkylidenecyclobutanols and their silyl ethers, J Am Chem Soc, 2005, 127 (32), 11206-7.

Jung, M. E. Piizzi, G. , gem-disubstituent effect: theoretical basis and synthetic applications, Chem Rev, 2005, 105 (5), 1735-66.

J. E. Katz, D. S. Dumlao, J. I. Wasserman, M. G. Lansdown, M. E. Jung, K. F. Faull and S. Clarke, 3-Isopropylmalate is the Major Endogenous Substrate of the Saccharomyces cerevisiae trans-Aconitate Methyltransferase, Biochemistry, 2004, 43, 5976-86.

M. E. Jung and A. Maderna, Allylation of Acetals and Ketals with Allyltrimethylsilane Catalyzed by the Mixed Lewis Acid System AlBr3/CuBr, Tetrahedron Lett., 2004, 45, 5301-04.

M. E. Jung and B. A. Duclos, Diastereoselectivity in the Carroll Rearrangement of β-Keto Esters of Tertiary Allylic Alcohols, Tetrahedron Lett., 2004, 45, 107-9.

Liew, C. K. Smith, B. T. Pilpa, R. Suree, N. Ilangovan, U. Connolly, K. M. Jung, M. E. Clubb, R. T. , Localization and mutagenesis of the sorting signal binding site on sortase A from Staphylococcus aureus, FEBS Lett, 2004, 571 (1-3), 221-6.

C. K. Liew, B. T. Smith, R. Pilpa, U. Ilangovan, K. M. Connolly, M. E. Jung, and R. T. Clubb, Localization and mutagenesis of the sorting signal binding site on sortase A from Staphylococcus aureus, FEBS Lett., 2004, 571, 221-226.

Jung, M. E. Maderna, A. , Microwave-assisted allylation of acetals with allyltrimethylsilane in the presence of CuBr, J Org Chem, 2004, 69 (22), 7755-7.

M. E. Jung and A. Maderna, Microwave-assisted Allylation of Acetals with Allyltrimethylsilane in the Presence of CuBr, J. Org. Chem., 2004, 69, 7755-57.

M. E. Jung and S.-J. Min, Novel Formation of a Bridged Bicyclic Furan by Rearrangement of a Tetrahydroxydecalinone, Tetrahedron Lett., 2004, 45, 6753-6755.

M. E. Jung, S.-J. Min, K. N. Houk, and D. Ess, Synthesis and Relative Stability of 3,5-Diacyl 4,5-Dihydro-1H-Pyrazoles Prepared by Dipolar Cycloaddition of Enones and α-Diazoketones, J. Org. Chem., 2004, 69, 9085-89.

Jung, M. E. Min, S. J. Houk, K. N. Ess, D. , Synthesis and relative stability of 3,5-diacyl-4,5-dihydro-1H-pyrazoles prepared by dipolar cycloaddition of enones and alpha-diazoketones, J Org Chem, 2004, 69 (26), 9085-9.

Jung, M. E. van den Heuvel, A. , A tandem non-aldol aldol Mukaiyama aldol reaction, Org Lett, 2003, 5 (24), 4705-7.

M. E. Jung and A. van den Heuvel, A tandem non-aldol aldol Mukaiyama aldol reaction, Org. Lett., 2003, 5, 4705-7.

M. E. Jung and J. I. Wasserman, Efficient Synthesis of Vinyl Chlorides and/or gem-Dichlorides from Ketones by Treatment with Tungsten Hexachloride, Tetrahedron Lett., 2003, 44, 7273-75.

M. E. Jung and G. Piizzi, First Synthesis of the A/B Ring of Ouabain, Organic Lett., 2003, 5, 137.

Jung, M. E. Piizzi, G. , First synthesis of the A/B ring of ouabain, Org Lett, 2003, 5 (2), 137-40.

Connolly, K. M. Smith, B. T. Pilpa, R. Ilangovan, U. Jung, M. E. Clubb, R. T. , Sortase from Staphylococcus aureus does not contain a thiolate-imidazolium ion pair in its active site, J Biol Chem, 2003, 278 (36), 34061-5.

K. M. Connolly, B. M. Smith, R. Pilpa, U. Ilangovan, M. E. Jung, and R. T. Clubb, Sortase from S. aureus Does not Contain a Thiolate-imidazolium Ion Pair in its Active Site, J. Biol. Chem., 2003, 278, 34061-34065.

M. E. Jung, A. Kers, G. Subbanagounder, and J. A. Berliner, Studies Towards the Total Synthesis of an Epoxy Isoprostane Phospholipid, a Potent Activator of Endothelial Cells, Chem. Commun., 2003, 167.

Jung, M. E. Kers, A. Subbanagounder, G. Berliner, J. A. , Studies towards the total synthesis of an epoxy isoprostane phospholipid, a potent activator of endothelial cells, Chem Commun (Camb), 2003, volume (2), 196-7.

Jung, M. Voit, S. Klimek, J. , Surface geometry of three packable and one hybrid composite after finishing, Oper Dent, 2003, 28 (1), 53-9.

Y. Nagao, C. Kimura, K. Kozawa, and M. E. Jung, Synthesis, Stereochemistry, and Reactions of 2,5-Diphenylsilacyclopentenes, Silicon Chem., 2003, 2, 99-107.

M. E. Jung and J. Pontillo, Synthetic Approach to Analogues of Sclerophytin A, Tetrahedron, 2003, 59, 2729.

M. E. Jung and G. Piizzi, Synthetic Approach to the AB Ring System of Ouabain, J. Org. Chem., 2003, 68, 2572-82.

Jung, M. E. Piizzi, G. , Synthetic approach to the AB ring system of ouabain, J Org Chem, 2003, 68 (7), 2572-82.

A. G. Leach, R. Wang, G. E. Wohlhieter, S. I. Khan, M. E. Jung, and K. N. Houk, Theoretical Elucidation of Kinetic and Thermodynamic Control of Radical Addition Regioselectivity, J. Am. Chem. Soc., 2003, 125, 4271-78.

Leach, A. G. Wang, R. Wohlhieter, G. E. Khan, S. I. Jung, M. E. Houk, K. N. , Theoretical elucidation of kinetic and thermodynamic control of radical addition regioselectivity, J Am Chem Soc, 2003, 125 (14), 4271-8.

M. E. Jung, A. van den Heuvel, A. G. Leach, and K. N. Houk, Unexpected Syn Hydride Migration in the Non-aldol Aldol Reaction, Organic Lett., 2003, 5, 3375-3378.

Jung, M. E. van den Heuvel, A. Leach, A. G. Houk, K. N. , Unexpected syn hydride migration in the non-aldol aldol reaction, Org Lett, 2003, 5 (19), 3375-8.

M. E. Jung, B. Hoffmann, B. Rausch, and J.-M. Contreras, Use of Hindered Silyl Ethers as Protecting Groups for the Non-Aldol Aldol Process, Organic Lett., 2003, 5, 3159-61.

Jung, M. E. Hoffmann, B. Rausch, B. Contreras, J. M. , Use of hindered silyl ethers as protecting groups for the non-aldol aldol process, Org Lett, 2003, 5 (17), 3159-61.

M. E. Jung and A. van den Heuvel, Diastereoselectivity in non-Aldol Aldol Reactions: Silyl Triflate Promoted Payne Rearrangements, Tetrahedron Lett., 2002, 43, 8169.

M. E. Jung and P. Davidov, Efficient Synthesis of a Tricyclic BCD Analogue of Ouabain: Lewis Acid Catalyzed Diels-Alder Reactions of Sterically Hindered Systems, Angew Chem., 2002, 41, 4125.

Jung, M. E. Davidov, P. , Efficient synthesis of a tricyclic BCD analogue of ouabain: Lewis acid catalyzed Diels-Alder reactions of sterically hindered systems, Angew Chem Int Ed Engl, 2002, 41 (21), 4125-8.

M. E. Jung and G. Piizzi, Novel Rearrangements of 4-Silyl-3-buten-2-ones, J. Org. Chem. , 2002, 67, 3911.

Jung, M. E. Piizzi, G. , Novel rearrangements of 4-silyl-3-buten-2-ones, J Org Chem, 2002, 67 (11), 3911-4.

M. E. Jung, A. Toyota, E. De Clercq, and J. Balzarini, Synthesis and Biological Activity of a Series of Methylene-Expanded Oxetanocin Nucleoside Analogues, Monatshefte Chem., 2002, 133, 499.

M. E. Jung and J. Pontillo, Synthetic Approach to Analogues of the Original Structure of Sclerophytin A, J. Org. Chem., 2002, 67, 6848.

Jung, M. E. Pontillo, J. , Synthetic approach to analogues of the original structure of sclerophytin A, J Org Chem, 2002, 67 (19), 6848-51.

Jung, M. E. Davidov, P. , Conclusive evidence of the trapping of primary ozonides, Org Lett, 2001, 3 (4), 627-9.

Cai, H. Strouse, J. Dumlao, D. Jung, M. E. Clarke, S. , Distinct reactions catalyzed by bacterial and yeast trans-aconitate methyltransferases, Biochemistry, 2001, 40 (7), 2210-9.

Jung, M. E. Nishimura, N. , Enantioselective formal total synthesis of (-)-dysidiolide, Org Lett, 2001, 3 (13), 2113-5.

Tantillo, D. J. Houk, K. N. Jung, M. E. , Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers, J Org Chem, 2001, 66 (6), 1938-40.

Jung, M. E. Toyota, A. , Preparation of 4'-substituted thymidines by substitution of the thymidine 5'-esters, J Org Chem, 2001, 66 (8), 2624-35.

Jung, M. E. Lee, C. P. , Synthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides, Org Lett, 2001, 3 (3), 333-6.

Jung, M. E. Davidov, P. , The first reported anionic oxy retro-ene reaction, Org Lett, 2001, 3 (19), 3025-7.

Jung, M. E. Marquez, R. , Efficient synthesis of the C(1)-C(11) fragment of the tedanolides. The nonaldol aldol process in synthesis, Org Lett, 2000, 2 (12), 1669-72.

Jung, M. E. Fahr, B. T. , Novel base-induced [1,2]-acyl shift of allylic esters of cyclopropanecarboxylic acids, J Org Chem, 2000, 65 (7), 2239-42.

Choe, S. W. Jung, M. E. , Preparation of various C-2 branched carbohydrates using intramolecular radical reactions, Carbohydr Res, 2000, 329 (4), 731-44.

Jung, M. E. Huang, A. Johnson, T. W. , Unusual Diastereoselectivity in Intramolecular Diels-Alder Reactions of Substituted 3,5-Hexadienyl Acrylates. Preference for a Boatlike Structure of the Six-Atom Tether Due to Ester Overlap, Org Lett, 2000, 2 (13), 1835-1837.

Jung, M. E. Lee, B. S. , Unusual alpha-methylation of alkoxyaryl ketones with higher order methyl cuprate and lithium bromide, J Org Chem, 2000, 65 (26), 9241-4.

Jung, M. E. Huang, A. , Use of optically active cyclic N,N-dialkyl aminals in asymmetric induction, Org Lett, 2000, 2 (17), 2659-61.