M E Jung

Summary

Affiliation: University of California
Country: USA

Publications

  1. ncbi request reprint Synthetic approach to analogues of the original structure of sclerophytin A
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095 1569, USA
    J Org Chem 67:6848-51. 2002
  2. ncbi request reprint Stepwise acid-promoted double-Michael process: an alternative to Diels-Alder cycloadditions for hindered silyloxydiene-dienophile pairs
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 9:375-8. 2007
  3. ncbi request reprint Versatile diastereoselectivity in formal [3,3]-sigmatropic shifts of substituted 1-alkenyl-3-alkylidenecyclobutanols and their silyl ethers
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Am Chem Soc 127:11206-7. 2005
  4. ncbi request reprint Intramolecular Diels-Alder reactions of optically active allenic ketones: chirality transfer in the preparation of substituted oxa-bridged octalones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, CA 90095 1569, USA
    J Am Chem Soc 127:10834-5. 2005
  5. ncbi request reprint Synthesis and relative stability of 3,5-diacyl-4,5-dihydro-1H-pyrazoles prepared by dipolar cycloaddition of enones and alpha-diazoketones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095 1569, USA
    J Org Chem 69:9085-9. 2004
  6. doi request reprint Trimethylaluminum-triflimide complexes for the catalysis of highly hindered Diels-Alder reactions
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA
    Org Lett 14:5169-71. 2012
  7. ncbi request reprint Microwave-assisted allylation of acetals with allyltrimethylsilane in the presence of CuBr
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Org Chem 69:7755-7. 2004
  8. ncbi request reprint Studies towards the total synthesis of an epoxy isoprostane phospholipid, a potent activator of endothelial cells
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Ave, Los Angeles, CA 90095, USA
    Chem Commun (Camb) . 2003
  9. ncbi request reprint Novel rearrangements of 4-silyl-3-buten-2-ones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095 1569, USA
    J Org Chem 67:3911-4. 2002
  10. doi request reprint Synthesis and duplex-stabilizing properties of fluorinated N-methanocarbathymidine analogues locked in the C3'-endo conformation
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 USA
    Angew Chem Int Ed Engl 53:9893-7. 2014

Research Grants

Collaborators

Detail Information

Publications70

  1. ncbi request reprint Synthetic approach to analogues of the original structure of sclerophytin A
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095 1569, USA
    J Org Chem 67:6848-51. 2002
    ..A two-step aldol process afforded the desired 3-pyrone 27 in good overall yield. However, several methods for the conversion of this enone 27 into the desired sclerophytin analogue 2 failed...
  2. ncbi request reprint Stepwise acid-promoted double-Michael process: an alternative to Diels-Alder cycloadditions for hindered silyloxydiene-dienophile pairs
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 9:375-8. 2007
    ..9:1 mixture of two cycloadducts. Hydrolysis of the major isomer gave the dione 27', a model for the BCD ring system of pentacyclic triterpenes. [reaction: see text]...
  3. ncbi request reprint Versatile diastereoselectivity in formal [3,3]-sigmatropic shifts of substituted 1-alkenyl-3-alkylidenecyclobutanols and their silyl ethers
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Am Chem Soc 127:11206-7. 2005
    ..Thus, the same starting material (e.g., 20) can be converted into either the exo or endo product, 22x or 22n, with good diastereocontrol by just changing the rearrangement conditions...
  4. ncbi request reprint Intramolecular Diels-Alder reactions of optically active allenic ketones: chirality transfer in the preparation of substituted oxa-bridged octalones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, CA 90095 1569, USA
    J Am Chem Soc 127:10834-5. 2005
    ..Thus, the optically active allenic ketone 20 afforded only the desired cycloadduct 21 with the correct absolute stereochemistry needed for the synthesis of the arisugacin class of natural products...
  5. ncbi request reprint Synthesis and relative stability of 3,5-diacyl-4,5-dihydro-1H-pyrazoles prepared by dipolar cycloaddition of enones and alpha-diazoketones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095 1569, USA
    J Org Chem 69:9085-9. 2004
    ..Thus we have discovered a novel fragmentation-cycloaddition process. We have also presented evidence for the mechanism of the formation of the dihydropyrazoles and carried out calculations to support these findings...
  6. doi request reprint Trimethylaluminum-triflimide complexes for the catalysis of highly hindered Diels-Alder reactions
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA
    Org Lett 14:5169-71. 2012
    ..Thus reaction of 1 with 2 afforded the hindered cycloadduct 4 in excellent yield in 0.5-1.5 h at -40 °C...
  7. ncbi request reprint Microwave-assisted allylation of acetals with allyltrimethylsilane in the presence of CuBr
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Org Chem 69:7755-7. 2004
    ..This method works best for aromatic acetals, giving the corresponding homoallyl ethers in good to quantitative yield...
  8. ncbi request reprint Studies towards the total synthesis of an epoxy isoprostane phospholipid, a potent activator of endothelial cells
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Ave, Los Angeles, CA 90095, USA
    Chem Commun (Camb) . 2003
    ....
  9. ncbi request reprint Novel rearrangements of 4-silyl-3-buten-2-ones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095 1569, USA
    J Org Chem 67:3911-4. 2002
    ..Two 4-silyl-3-buten-2-ones, 2a and 2c, underwent an interesting rearrangement involving migration of the allyl or phenyl group on the silicon atom to the adjacent enone carbon when treated with various bases...
  10. doi request reprint Synthesis and duplex-stabilizing properties of fluorinated N-methanocarbathymidine analogues locked in the C3'-endo conformation
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 USA
    Angew Chem Int Ed Engl 53:9893-7. 2014
    ..We show that 2'-F incorporation on the N-MCT scaffold has a strong stabilizing effect on duplex thermal stability. ..
  11. doi request reprint Studies toward the enantiospecific total synthesis of rhodexin A
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Org Chem 78:7518-26. 2013
    ....
  12. doi request reprint Se-Phenyl Prop-2-eneselenoate: An Ethylene Equivalent for Diels-Alder Reactions
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 1569 USA
    Angew Chem Int Ed Engl 52:2060-2. 2013
    ..Its cycloadducts 3 with many dienes 1 can be easily reduced to the hydrocarbons 4 under radical conditions. This process works even in cases where there is an adjacent group that can be easily eliminated, e.g., an allylic ether...
  13. pmc Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl α-ketoglutarate
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Org Chem 77:11002-5. 2012
    ..This is a cell-permeable prodrug form of α-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right...
  14. ncbi request reprint Total synthesis of the proposed structure of mycosporulone: structural revision and an unexpected retro-aldol/aldol reaction
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 14:4898-901. 2012
    ..The spectroscopic data for both 1 and its C2 epimer 1a did not match those reported for the natural product. A revised structure 29 for mycosporulone is proposed...
  15. doi request reprint Synthesis of a trans,syn,trans-dodecahydrophenanthrene via a bicyclic transannular Diels-Alder reaction: intermediate for the synthesis of fusidic acid
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E Young Drive, Los Angeles, California 90095 1569, USA
    J Org Chem 75:6933-40. 2010
    ..Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does...
  16. ncbi request reprint Synthesis of the C1-C12 fragment of the tedanolides. Aldol-non-aldol aldol approach
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 9:3543-6. 2007
    ..The combination of highly stereoselective non-aldol aldol and aldol processes allows the preparation of the completely protected C1-C12 fragment 2 of the novel macrocyclic cytotoxic agent tedanolide 1...
  17. ncbi request reprint Total synthesis of (+/-)-hedychilactone B: stepwise allenoate diene cycloaddition to prepare trimethyldecalin systems
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 9:461-3. 2007
    ....
  18. ncbi request reprint Total synthesis of (+/-)-hedychenone: trimethyldecalin terpene systems via stepwise allenoate diene cycloaddition
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA
    Org Lett 8:5857-9. 2006
    ..The exo isomer 4x was converted in four steps (reduction, oxidation, olefination, and desilylation) into hedychenone 1. [reaction: see text]..
  19. ncbi request reprint Practical syntheses of dyes for difference gel electrophoresis
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Ave, Los Angeles, CA 90095, USA
    Bioorg Med Chem 14:92-7. 2006
    ....
  20. ncbi request reprint Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Ave, Los Angeles, CA 90095, USA
    Bioorg Med Chem Lett 15:5076-9. 2005
    ....
  21. ncbi request reprint Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC
    Michael E Jung
    Departments of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, CA 90095, USA
    Org Lett 7:3933-5. 2005
    ..Final coupling with lyso-PC 16 and silyl group deprotection gave PECPC 2 and PEIPC 1, which showed the same activity as natural PECPC and PEIPC. [reaction: see text]..
  22. ncbi request reprint Anti aldol selectivity in a synthetic approach to the C1-C12 fragment of the tedanolides
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 10:137-40. 2008
    ....
  23. doi request reprint Facile synthesis of cis-2-Alkyl-3-trialkylsilyloxycycloalkanones via the non-aldol aldol rearrangement of 2,3-epoxycycloalkanols
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 10:2039-41. 2008
    ..g., tert-butyl. Finally, it has been shown that the stereochemistry of the epoxy alcohol is crucial as one would expect from the mechanism...
  24. doi request reprint Preparation of a functionalized tetracyclic intermediate for the synthesis of rhodexin A
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 10:3647-9. 2008
    ..This compound was then transformed into the methylated enedione 13 which afforded after a reductive alkylation and annulation sequence the tetracycle 19...
  25. doi request reprint Enantiospecific formal total synthesis of (+)-fawcettimine
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 12:2962-5. 2010
    ..The analogous cyclization of 33, the diastereomer of 27, afforded the diastereomeric diester 34, thereby demonstrating that the cyclization process is diastereospecific...
  26. pmc Total synthesis of auripyrone B using a non-aldol aldol-cuprate opening process
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 12:2872-5. 2010
    ..This compound was used for an efficient synthesis of the natural product auripyrone B 2 in only 20 steps and 8% overall yield from 14 using a late-stage spiroketalization onto a stable hemiketal as the final key step...
  27. pmc Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC)
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA
    J Med Chem 53:2779-96. 2010
    ..A structure-activity relationship study was carried out on a series of thiohydantoins and their analogues 14 which led to the discovery of 92 (MDV3100) as the clinical candidate for the treatment of hormone refractory prostate cancer...
  28. doi request reprint Total synthesis of racemic laurenditerpenol, an HIF-1 inhibitor
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90064 1569, USA
    J Org Chem 74:8739-53. 2009
    ..The aldehyde 54 was prepared by ring-opening and elaboration of lactone 41. In addition, four analogues of 1 were also successfully synthesized for biological testing...
  29. doi request reprint Studies toward the total syntheses of cucurbitacins B and D
    Michael E Jung
    Department of Chemistry, Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Org Chem 75:7146-58. 2010
    ..The diastereomer of the core of the cucurbitacins, epimeric at C8, C9, and C10, 51, was synthesized via a highly regio- and stereoselective Diels-Alder reaction of the diene 4 and the novel dienophile 50...
  30. doi request reprint First total synthesis of rhodexin A
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States
    Org Lett 13:2698-701. 2011
    ..This compound was then transformed into the tetracyclic enone 16, which was converted to rhodexin A (1)...
  31. doi request reprint Total synthesis of (+/-)-kellermanoldione: stepwise cycloaddition of a functionalized diene and allenoate
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 11:3882-5. 2009
    ..It was converted into 1 via six steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether...
  32. doi request reprint An efficient synthesis of the protected carbohydrate moiety of Brasilicardin A
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 13:3710-3. 2011
    ..The imidate 2 was coupled via TMSOTf-mediated glycosidation with cholesterol as a model aglycone followed by the selective cleavage of all the acetate groups to give the Brasilicardin A analogue 16...
  33. pmc Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines
    Michael E Jung
    Departments of Chemistry and Biochemistry, Medicine Cardiology, and Pathology, University of California, Los Angeles, California 90095, USA
    Org Lett 10:4207-9. 2008
    ..Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles...
  34. doi request reprint Synthesis and evaluation of compounds that induce readthrough of premature termination codons
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Ave, Los Angeles, CA 90095, United States
    Bioorg Med Chem Lett 21:5842-8. 2011
    ..In addition, hypothesizing that these compounds exhibit their activity by binding to the ribosome, we prepared the hybrid analogs 13 containing pyrimidine bases and these also showed good readthrough activity...
  35. pmc Synthesis of 2-substituted 7-hydroxybenzofuran-4-carboxylates via addition of silyl enol ethers to o-benzoquinone esters
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 11:2165-7. 2009
    ..Alkyl and aryl systems work well, but highly electron-rich silyl enol ethers could not be used because of competing oxidation...
  36. ncbi request reprint First synthesis of the A/B ring of ouabain
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 5:137-40. 2003
    ..A key Robinson annulation allows for the building of the desired carbon framework in one high-yielding step. Directed epoxidation followed by selective epoxide opening furnished the final tetraol with the desired all-cis stereochemistry...
  37. ncbi request reprint Synthetic approach to the AB ring system of ouabain
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095 1569, USA
    J Org Chem 68:2572-82. 2003
    ..Finally a novel rearrangement was observed when the epoxy alcohol 24 was treated with DIBAL to effect loss of the angular hydroxymethyl group to produce the tetrasubstitued alkene 29 in high yield...
  38. ncbi request reprint Enantioselective formal total synthesis of (-)-dysidiolide
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 3:2113-5. 2001
    ..reaction: see text] An enantioselective formal total synthesis of the sesterterpene (-)-dysidiolide 1 beginning with an intermolecular Diels-Alder reaction of the allene ester 3 and the silyloxydiene 10 is reported...
  39. ncbi request reprint Efficient synthesis of 2-deoxy L-ribose from L-arabinose: mechanistic information on the 1,2-acyloxy shift in alkyl radicals
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095 1569, USA
    Org Lett 1:1517-9. 1999
    ..It has been shown that the similar dialkoxyalkyl radical IV is not an intermediate in the 1,2-acyloxy shift of anomeric radical I...
  40. ncbi request reprint Efficient synthesis of a tricyclic BCD analogue of ouabain: Lewis acid catalyzed Diels-Alder reactions of sterically hindered systems
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 405 Hilgard Ave, Los Angeles, CA 90095 1569, USA
    Angew Chem Int Ed Engl 41:4125-8. 2002
  41. ncbi request reprint First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095 1569, USA
    Org Lett 1:1671-4. 1999
    ..The key steps of the synthesis are the Breslow remote functionalization of the polyoxygenated steroid derived from 25 and the base-catalyzed epimerization-aldol condensation of the dione derived from 27...
  42. ncbi request reprint Efficient synthesis of the C(1)-C(11) fragment of the tedanolides. The nonaldol aldol process in synthesis
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095 1569, USA
    Org Lett 2:1669-72. 2000
    ..The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions...
  43. ncbi request reprint The first reported anionic oxy retro-ene reaction
    M E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA
    Org Lett 3:3025-7. 2001
    ..Mechanistic analysis reveals that this is the first case of an anionic oxy retro-ene reaction followed by a tandem intramolecular aldol condensation. Reaction: see text...
  44. ncbi request reprint Synthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 3:333-6. 2001
    ..figure: see text] The use of several non-aldol aldol processes allows one to prepare a fully functionalized and completely protected C1-C11 fragment that should be useful for the total synthesis of the tedanolides...
  45. ncbi request reprint Use of optically active cyclic N,N-dialkyl aminals in asymmetric induction
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095 1569, USA
    Org Lett 2:2659-61. 2000
    ....
  46. ncbi request reprint Preparation of 4'-substituted thymidines by substitution of the thymidine 5'-esters
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 1569, USA
    J Org Chem 66:2624-35. 2001
    ....
  47. ncbi request reprint Conclusive evidence of the trapping of primary ozonides
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095, USA
    Org Lett 3:627-9. 2001
    ..The proposed mechanism involves an unusual trapping of the primary ozonide that undergoes a Grob-like fragmentation instead of dissociating into the Criegee intermediates...
  48. ncbi request reprint Synthesis of highly substituted cyclohexenes via mixed Lewis acid-catalyzed Diels-Alder reactions of highly substituted dienes and dienophiles
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA
    Org Lett 7:1649-51. 2005
    ..Thus, reaction of the hindered diene 4 with various substituted enones gave good yields of the expected cycloadducts even though both partners are quite sterically hindered...
  49. ncbi request reprint Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90064 1569, USA
    J Org Chem 72:8565-8. 2007
    ..We report the structure determination of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably promoted by an acidic substance, and propose a reasonable mechanism for its formation...
  50. ncbi request reprint Synthesis of four diastereomeric 3,5-dialkoxy-2,4-dimethylalkanals by a simple extension of the non-aldol aldol process to bis(propionates)
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095 1569, USA
    Org Lett 1:307-9. 1999
    ..The epoxy mesylates (13, 16) gave the desired products (14, 17) in good yield on treatment with TMSOTf and a hindered base...
  51. ncbi request reprint A tandem non-aldol aldol Mukaiyama aldol reaction
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 5:4705-7. 2003
    ..The diastereoselectivity changes to an anti preference for most aldehydes. This anti selectivity overwhelms the normal Felkin-Ahn preference; namely, the 1,5-anti isomer predominates even when it is anti-Felkin-Ahn...
  52. ncbi request reprint Unexpected syn hydride migration in the non-aldol aldol reaction
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Org Lett 5:3375-8. 2003
    ..Calculations suggest that this unusual reaction proceeds via the carbocation, which cannot easily rotate due to steric hindrance...
  53. ncbi request reprint Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols
    M E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles 90095 1569, USA
    Org Lett 1:367-9. 1999
    ..This reaction has been extended to the preparation of homoallylic hydroxyketones from allylic alcohols by reaction with 6 and the rhodium catalyst...
  54. ncbi request reprint Use of hindered silyl ethers as protecting groups for the non-aldol aldol process
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095 1569, USA
    Org Lett 5:3159-61. 2003
    ..g., 16, with little to none of the corresponding tetrahydrofurans...
  55. ncbi request reprint Sortase from Staphylococcus aureus does not contain a thiolate-imidazolium ion pair in its active site
    Kevin M Connolly
    Department of Chemistry and Biochemistry, Molecular Biology Institute and UCLA Department of Energy Institute for Genomics and Proteomics, UCLA, Los Angeles, California 90095 1570, USA
    J Biol Chem 278:34061-5. 2003
    ..4 and 7.0, respectively. These measurements are inconsistent with the existence of a thiolate-imidazolium ion pair and suggest a general base catalysis mechanism during transpeptidation...
  56. ncbi request reprint Distinct reactions catalyzed by bacterial and yeast trans-aconitate methyltransferases
    H Cai
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    Biochemistry 40:2210-9. 2001
    ....
  57. ncbi request reprint Structural identification of a novel pro-inflammatory epoxyisoprostane phospholipid in mildly oxidized low density lipoprotein
    A D Watson
    Department of Medicine, University of California, Los Angeles, California 90095, USA
    J Biol Chem 274:24787-98. 1999
    ..The identification of this molecule adds epoxyisoprostanes to the growing list of biologically active isoprostanes...
  58. ncbi request reprint Theoretical elucidation of kinetic and thermodynamic control of radical addition regioselectivity
    Andrew G Leach
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1569, USA
    J Am Chem Soc 125:4271-8. 2003
    ..Experimental studies revealed that the reaction yields only the products of 6-endo cyclization through kinetic control...
  59. ncbi request reprint Recent advances towards new anti-infective agents that inhibit cell surface protein anchoring in Staphylococcus aureus and other gram-positive pathogens
    N Suree
    Department of Chemistry and Biochemistry, Molecular Biology Institute, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095 1570, USA
    Mini Rev Med Chem 7:991-1000. 2007
    ..Here we review what is known about the mechanism of sortase mediated protein anchoring and discuss recently identified inhibitors of this new important enzyme family...
  60. ncbi request reprint Localization and mutagenesis of the sorting signal binding site on sortase A from Staphylococcus aureus
    Chu Kong Liew
    Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095 1570, USA
    FEBS Lett 571:221-6. 2004
    ..Compatible with its recently proposed role as a general base, R197 is also shown to be required for catalysis...
  61. ncbi request reprint Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers
    D J Tantillo
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA
    J Org Chem 66:1938-40. 2001
    ....
  62. ncbi request reprint Preparation of various C-2 branched carbohydrates using intramolecular radical reactions
    S W Choe
    Department of Chemistry and Biochemistry, Loyola Marymount University, Los Angeles, CA 90045 8225, USA
    Carbohydr Res 329:731-44. 2000
    ..This method was extended to synthesize a beta C-2 branched glucopyranoside, a C-2 branched galactoside and a C-2 cyano glucopyranoside...
  63. pmc Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors
    Nuttee Suree
    Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 1570, USA
    Bioorg Med Chem 17:7174-85. 2009
    ..Many of these molecules also inhibit the sortase enzyme from Bacillus anthracis suggesting that they may be generalized sortase inhibitors...
  64. pmc The structure of the Staphylococcus aureus sortase-substrate complex reveals how the universally conserved LPXTG sorting signal is recognized
    Nuttee Suree
    Department of Chemistry and Biochemistry, UCLA, Los Angeles, California 90095 1570, USA
    J Biol Chem 284:24465-77. 2009
    ..Since the sortase-catalyzed anchoring reaction is required for the virulence of a number of bacterial pathogens, the results presented here may facilitate the development of new anti-infective agents...
  65. ncbi request reprint Staphylococcus aureus Sortase A transpeptidase. Calcium promotes sorting signal binding by altering the mobility and structure of an active site loop
    Mandar T Naik
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095 1570, USA
    J Biol Chem 281:1817-26. 2006
    ....
  66. doi request reprint Use of 4-cyanocoumarins as dienophiles in a facile synthesis of highly substituted dibenzopyranones
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA
    Org Lett 11:757-60. 2009
    ....
  67. ncbi request reprint 3-Isopropylmalate is the major endogenous substrate of the Saccharomyces cerevisiae trans-aconitate methyltransferase
    Jonathan E Katz
    Department of Chemistry and Biochemistry, The Molecular Biology Institute, Los Angeles, California 90095 1570, USA
    Biochemistry 43:5976-86. 2004
    ....
  68. ncbi request reprint gem-disubstituent effect: theoretical basis and synthetic applications
    Michael E Jung
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095 1569, USA
    Chem Rev 105:1735-66. 2005
  69. pmc A broad-spectrum antiviral targeting entry of enveloped viruses
    Mike C Wolf
    Department of Microbiology, Immunology, and Molecular Genetics, University of California, Los Angeles, CA 90025, USA
    Proc Natl Acad Sci U S A 107:3157-62. 2010
    ..In sum, our data reveal a class of broad-spectrum antivirals effective against enveloped viruses that target the viral lipid membrane and compromises its ability to mediate virus-cell fusion...
  70. pmc Composite synthetic lethal identification of membrane traffic inhibitors
    Mara C Duncan
    Department of Biological Chemistry, David Geffen School of Medicine, University of California, Los Angeles, CA 90095, USA
    Proc Natl Acad Sci U S A 104:6235-40. 2007
    ..Furthermore, the easily automated technology should be adaptable for identification of inhibitors of other cellular processes...

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