Michael E. Jung

B.S. 1969, Rice University; Ph.D. 1973, Columbia University; NATO Postdoctoral, 1973-4, ETH, Zürich; Fulbright-Hays Senior Research Scholar,1980-8l; Alfred P. Sloan Fellow, 1979-8l; Camille and Henry Dreyfus Teacher-Scholar, 1978-83; UCLA Distinguished Teaching Award, 1978; Inaugural UCLA Gold Shield Faculty Prize, 1986-8; Glenn T. Seaborg Award, 1987; Fujii-Ohtsuka Professor, Tokushima University, 1991; UCLA McCoy Award, 1991-2; UCLA Hanson-Dow Teaching Award, 1992; American Chemical Society Arthur C. Cope Scholar Award, 1995..

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RESEARCH INTERESTS

Antitumor and Antiviral Agents

At present we are engaged in the total synthesis of a large number of active antitumor and antiviral agents. The current cytotoxic targets include dichlorolissoclimide, tedanolide and 13-deoxytedanolide, aplysiapyranoids A-D, discodermide, dysidiolide, sclerophytin A, cylindramide A, and halomon and its alkene derivatives. The antiviral compounds are oxetanocin A and its analogues, both the carbocyclic ones, e.g., cyclobut-A and G, and the C-oxetanocins (related to oxetanocin H), methylene-expanded oxetanocins, several modified N-nucleosides (2',3'-dideoxycytidine and analogues, AZT, d4T and their analogues, l-3-TC), carbovir, and the cyclophellitols. We are also investigating new methods for the preparation of l-carbohydrates and their corresponding modified nucleosides, e.g., l-5-F ddC, which have shown strong antiviral activity. As possible reagents for antisense oligonucleotide therapy, we are preparing both l-DNA and l-RNA. Finally we are preparing several isonucleosides and 4'-substituted 2'-deoxynucleosides as potential antiviral agents.


 

 Other Biologically Active Compounds

The synthesis of several biologically active alkaloids is currently under investigation. Included among our synthetic goals are the following: the novel dimeric bis-amino acid isodityrosine, the antitumor agents bouvardin and deoxybouvardin, the ACE inhibitor K-13, the platelet aggregation inhibitor herquline, and the antifungal agent piperazinomycin. We are also pursuing total syntheses of some antiulcer compounds (the plaunol class of clerodane diterpenes), antiinflammatory agents (pseudopterosin A), and the unusual ketosterols xestobergsterol and contignasterol, which are inhibitors of histamine release. We are developing new processes for the efficient synthesis of various cardioactive agents, e.g., ouabain and several naturally occurring natriuretic agents. We have several collaborative programs, e.g., to prepare modified peptides as potential inhibitors of carboxy methyl transferases, to develop a new method of delivering antibacterial agents to resistant bacterial strains, and finally to determine the structures and mechanism of action of several naturally occurring natriuretic agents.

 New Synthetic Methods and Physical Organic Chemistry

We are studying several epoxide rearrangements, e.g., the preparation of asymmetric quaternary aldehydes from tertiary vinyl oxiranes. By this method, we have also determined that a benzylic cation is more stable than an allylic one, e.g., the ethenyl phenyl oxirane gave the single optically active product shown below. We have also developed a new method for the preparation of aldols by a non-aldol process.

Thus conversion of an aldehyde to the epoxy alcohol via Wittig reaction and reduction followed by Sharpless epoxidation generates the substrate for the rearrangement which is effected by treatment with trialkylsilyl triflates and base to give the protected aldol products in high yield. We are now extending this reaction to the synthesis of polypropionates by an iterative process so that compounds such as erythromycin and rifamycin could be prepared.

 We are also studying the use of radical cyclization-fragmentation processes for the synthesis of several natural products of biological interest. Finally, we are investigating the synthetic potential of substituent effects (gem-dialkyl, -dialkoxy, -dithioalkoxy, -dicarboalkoxy, bis(dialkylamino), etc.) and polar solvent effects on cyclizations, including the novel acceleration of the intramolecular Diels-Alder reactions of furfuryl methyl fumarates by the use of polar solvents. Dialkoxy substitution, both gem and vic, allows one to carry out a wide variety of cyclizations, including cyclizations to produce 4- and 8-membered rings. We are also studying the possibility of asymmetric induction in these processes.

 

RECENT PUBLICATIONS of the Jung Group

Jung ME, Kim WJ "Practical Syntheses of Dyes for Difference Gel Electrophoresis" Bioorg. & Med. Chem., 2006, 14, 92-.

Jung ME, Min SJ "Intramolecular Diels-Alder Reactions of Optically Active Allenic Ketones: Chirality Transfer in the Preparation of Substituted Oxa-Bridged Octalones (vol 127, pg 10834, 2005)" J. Am. Chem. Soc., 2005, 127, 16338-16338.

Jung ME, Novack AR "Formation of 3,4-dimethyl-2-pyrones from allene carboxylates and 2-silyloxydienes via 3-carboethoxyethylidene cyclobutanols
Tet. Lett., 2005, 46, 8237-8240.

Jung ME, Clemens JJ, Suree N, et al. "Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a Threonine Analogue for Covalent Inhibition of Sortases" Bioorg. & Med. Chem., Lett., 2005, 15, 5076-5079.

Jung ME, Berliner JA, Angst D, et al. "Total synthesis of the Epoxy Isoprostane Phospholipids PEIPC and PECPC" Org. Lett., 2005, 7, 3933-3935.

Jung ME, Nishimura N, Novack AR "Versatile diastereoselectivity in Formal [3,3]-Sigmatropic Shifts of Substituted 1-Alkenyl-3-Alkylidenecyclobutanols and Their Silyl Ethers"
J. Am. Chem. Soc., 2005, 127, 11206-11207.

Jung ME, Min SJ "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, 10834-10835.

Jung ME, Maderna A "Synthesis of bicyclo[2.2.2]oct-5-en-2-ones Via a Tandem Intermolecular Michael Addition Intramolecular Aldol Process (A Bridged Robinson Annulation)" Tet. Lett., 2005, 46, 5057-5061.

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

Jung ME, Ho D, Chu HFV "Synthesis of Highly Substituted Cyclohexenes Via Mixed Lewis Acid-Catalyzed Diels-Alder Reactions of Highly Substituted Dienes and Dienophiles" Org. Lett., 2005, 7, 1649-1651.

Jung ME, Jung ME, Min SJ, Houk KN, 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, 9085-9089

Jung ME, Maderna A "Microwave-assisted allylation of acetals with allyltrimethylsilane in the presence of CuBr " J. Org. Chem., 2004, 69, 7755-7757.

Jung ME, Min SJ "Novel formation of a bridged bicyclic furan by rearrangement of a tetrahydroxydecalinone" Tet. Letts., 2004, 45, 6753-6755.

Liew CK, Smith BT, Pilpa R, Suree N, Ilangovan U, Connolly KM, Jung ME, Clubb RT "Localization and mutagonesis of the sorting signal binding site on sortase A from Staphylococcus aureus" Febs Letts., 2004, 571, 221-226.

Jung ME, Maderna "Allylation of acetals and ketals with allyltrimethylsilane catalyzed by the mixed Lewis acid system AlBr3/CuBr " Tet. Letts., 2004, 455301-5304.

Jonathan E. Katz, Darren S. Dumlao, Jacob I. Wasserman, Michael G. Lansdown, Michael E. Jung, Kym F. Faull, and Steven Clarke "3-isopropylmalate is the major endogenous substrate of the Saccharomyces cerevisiae trans-aconitate methyltransferase" Biochem., 2004, 43. (20): 5976-5986.

Lansdown MG, Jung ME "Progress toward the total synthesis of Brasilicardin A" Abstracts Of Papers Of The Amer. Chem. Soc., 2003, 225, U351-U351 422-ORGN Part 2

Jung ME, Min SJ "Progress toward the synthesis of arisugacins and territrems" Abstracts of Papers of Amer., Chem. Soci., 2003, 226, U143-U143 190-Orgn Part 2

Wasserman JI, Jung ME "Progress toward the total synthesis of reticulidin A and deoxyreticulidin A" Abstracts Of Papers Of The Amer. Chem. Soc., 2003, 226, U146-U147 208-ORGN Part 2.

Jung ME, Duclos BA "Diastereoselectivity in the Carroll rearrangement of beta-keto esters of tertiary allylic alcohols" Tet. Letts., 2004, 45, 107-109.

Jung ME, van den Heuvel A "A tandem non-aldol aldol Mukaiyama aldol reaction" Org. Letts., 5, 2003, 4705-4707 NOV 27

Jung ME, Wassermann JI "Efficient synthesis of vinyl chlorides and/or gem-dichlorides from ketones by treatment with tungsten hexachloride
Tet. Letts., 2003, 44 , 7273-7275.


Jung ME, van den Heuvel A, Leach AG, Houk KN "Unexpected syn hydride migration in the non-aldol aldol reaction " Org. Letts., 2003, 5, 3375-3378.

Connolly KM, Smith BT, Pilpa R, Ilangovan U, Jung ME, Clubb RT "Sortase from Staphylococcus aureus does not contain a thiolate-imidazolium ion pair in its active site" J. Biol. Chem., 2003, 278.

Michael E. Jung,* Barbara Hoffmann, Bernhard Rausch, and Jean-Marie Contreras "Use of hindered silyl ethers as protecting groups for the non-aldol aldol process" Org. Letts., 2003, 5, 3159-3161.

Jung ME, Pontillo J "Synthetic approach to potential precursors of sclerophytin A" Tet., 2003 59. (15): 2729-2736.

Leach AG, Wang RX, Wohlhieter GE, Khan SI, Jung ME, Houk KN
"Theoretical elucidation of kinetic and thermodynamic control of radical addition regioselectivity" J. Amer. Chem. Soc., 2003, 125, 4271-4278.

Jung ME, Piizzi G "Synthetic approach to the AB ring system of ouabain
J. Org. Chem., 2003, 68, 2572-2582.

Jung ME, Piizzi G "First synthesis of the A/B ring of ouabain"
Org. Letts., 2003, 5, 137-140

Jung ME, Kers A, Subbanagounder G, Berliner JA "Studies Towards the Total Synthesis of an Epoxy Isoprostane Phospholipid, A Potent Activator of Endothelial Cells" Chem. Comms., 2003, 196-197

Jung ME, Davidov P "Efficient Synthesis of A Tricyclic BCD Analogue of Ouabain: Lewis Acid Catalyzed Diels-Alder Reactions of Sterically Hindered Systems" Angewandte Chemie-Int. Ed., 2002, 41, 4125-4128

Jung ME, van den Heuvel A "Diastereoselectivity in Non-Aldol Aldol Reactions: Silyl Triflate-Promoted Payne Rearrangements" Tet. Letts.. 2002, 43 , 8169-8172 .

Jung ME, Pontillo J "Synthetic Approach to Analogues of the Original Structure of Sclerophytin A" J. Org. Chem., 2002, 67, (19): 6848-6851.

Jung ME, van den Heuvel A "Tandem Non-Aldol Aldol Mukaiyama Aldol Reaction" Abstracts of Papers Of The Amer. Chem.Soc., 2002, 224: 541-ORGN Part 2.

 

TOTAL PUBLICATIONS

ADDITIONAL INFORMATION

The Jung Research Group Page

Email: jung@chem.ucla.edu
Phone: 310-825-7954
Fax: 310-206-3722
  
University of California, Los Angeles
Department of Chemistry and Biochemistry
607 Charles E. Young Drive East
Los Angeles, CA 90095-1569

Updated on 8/29/06