Dirk Menche

Summary

Affiliation: University of Heidelberg
Country: Germany

Publications

  1. doi Modular total synthesis of archazolid A and B
    Dirk Menche
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, Im Neuenheimer Feld 270, D 69120 Heidelberg
    J Org Chem 74:7220-9. 2009
  2. doi Design, synthesis and biological evaluation of simplified analogues of the RNA polymerase inhibitor etnangien
    Dirk Menche
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120 Heidelberg, Germany
    Bioorg Med Chem Lett 20:939-41. 2010
  3. doi New methods for stereochemical determination of complex polyketides: configurational assignment of novel metabolites from myxobacteria
    Dirk Menche
    Department of Organic Chemistry, University of Heidelberg, Heidelberg, Germany
    Nat Prod Rep 25:905-18. 2008
  4. doi Stereochemical determination and complex biosynthetic assembly of etnangien, a highly potent RNA polymerase inhibitor from the myxobacterium Sorangium cellulosum
    Dirk Menche
    University of Heidelberg, Department of Organic Chemistry, INF 270, D 69120 Heidelberg, Germany
    J Am Chem Soc 130:14234-43. 2008
  5. doi Stereoselective total synthesis of etnangien and etnangien methyl ester
    Pengfei Li
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, Im Neuenheimer Feld 270, D 69120 Heidelberg, Germany
    J Org Chem 75:2429-44. 2010
  6. doi Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic etnangien by a flexible coupling strategy based on hetero-bis-metallated alkenes
    Mario Altendorfer
    University of Heidelberg, Department of Organic Chemistry, INF 270, D 69120 Heidelberg, Germany, EU
    Org Biomol Chem 11:2116-39. 2013
  7. doi Concise synthesis of the macrocyclic core of rhizopodin by a Heck macrocyclization strategy
    Michael Dieckmann
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120, Heidelberg, Germany
    J Org Chem 77:10782-8. 2012
  8. doi Total synthesis of etnangien
    Pengfei Li
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120 Heidelberg, Germany
    J Am Chem Soc 131:11678-9. 2009
  9. doi Synthesis and biological evaluation of a water-soluble derivative of the potent V-ATPase inhibitor archazolid
    Elke Persch
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, 69120 Heidelberg, Germany
    Bioorg Med Chem Lett 22:7735-8. 2012
  10. doi Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
    Michael Dieckmann
    Universitat Heidelberg, Institut fur Organische Chemie, INF 270, D 69120 Heidelberg, Germany
    Org Lett 15:228-31. 2013

Collaborators

Detail Information

Publications33

  1. doi Modular total synthesis of archazolid A and B
    Dirk Menche
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, Im Neuenheimer Feld 270, D 69120 Heidelberg
    J Org Chem 74:7220-9. 2009
    ..The expedient and flexible strategy will enable further SAR studies of the archazolids and more detailed evaluations of target-inhibitor interactions...
  2. doi Design, synthesis and biological evaluation of simplified analogues of the RNA polymerase inhibitor etnangien
    Dirk Menche
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120 Heidelberg, Germany
    Bioorg Med Chem Lett 20:939-41. 2010
    ..Novel simplified analogues of the potent RNA polymerase inhibitor etnangien were obtained by total synthesis and evaluated for antibacterial activity against Gram-positive bacteria and one Gram-negative bacterium...
  3. doi New methods for stereochemical determination of complex polyketides: configurational assignment of novel metabolites from myxobacteria
    Dirk Menche
    Department of Organic Chemistry, University of Heidelberg, Heidelberg, Germany
    Nat Prod Rep 25:905-18. 2008
    ..These methods are presented in their applications to structurally novel polyketide classes from myxobacteria...
  4. doi Stereochemical determination and complex biosynthetic assembly of etnangien, a highly potent RNA polymerase inhibitor from the myxobacterium Sorangium cellulosum
    Dirk Menche
    University of Heidelberg, Department of Organic Chemistry, INF 270, D 69120 Heidelberg, Germany
    J Am Chem Soc 130:14234-43. 2008
    ....
  5. doi Stereoselective total synthesis of etnangien and etnangien methyl ester
    Pengfei Li
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, Im Neuenheimer Feld 270, D 69120 Heidelberg, Germany
    J Org Chem 75:2429-44. 2010
    ..The expedient and flexible strategy of the etnangiens should be amenable to designed analogues of these RNA-polymerase inhibitors, thus enabling further exploration of the promising biological potential of these macrolide antibiotics...
  6. doi Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic etnangien by a flexible coupling strategy based on hetero-bis-metallated alkenes
    Mario Altendorfer
    University of Heidelberg, Department of Organic Chemistry, INF 270, D 69120 Heidelberg, Germany, EU
    Org Biomol Chem 11:2116-39. 2013
    ....
  7. doi Concise synthesis of the macrocyclic core of rhizopodin by a Heck macrocyclization strategy
    Michael Dieckmann
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120, Heidelberg, Germany
    J Org Chem 77:10782-8. 2012
    ....
  8. doi Total synthesis of etnangien
    Pengfei Li
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120 Heidelberg, Germany
    J Am Chem Soc 131:11678-9. 2009
    ..The convergent approach should be amenable to designed analogues...
  9. doi Synthesis and biological evaluation of a water-soluble derivative of the potent V-ATPase inhibitor archazolid
    Elke Persch
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, 69120 Heidelberg, Germany
    Bioorg Med Chem Lett 22:7735-8. 2012
    ..The first water-soluble analogue was then designed, synthesized, and evaluated for V-ATPase inhibitory activity in vitro...
  10. doi Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
    Michael Dieckmann
    Universitat Heidelberg, Institut fur Organische Chemie, INF 270, D 69120 Heidelberg, Germany
    Org Lett 15:228-31. 2013
    ..The sequence proceeds with excellent anti-selectivities and enables the rapid construction of complex polyketide fragments...
  11. doi Full stereochemical determination of ajudazols A and B by bioinformatics gene cluster analysis and total synthesis of ajudazol B by an asymmetric ortholithiation strategy
    Sebastian Essig
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
    J Am Chem Soc 134:19362-5. 2012
    ....
  12. doi Design, synthesis and biological evaluation of simplified side chains of the macrolide antibiotic etnangien
    Mario Altendorfer
    Organische Chemie, Ruprecht Karls Universitat Heidelberg, INF 270, D 69120 Heidelberg, Germany
    Bioorg Med Chem Lett 22:5731-4. 2012
    ..Novel simplified side chains of the potent RNA polymerase inhibitor etnangien were designed, synthesized and evaluated for antibacterial activity against Gram-positive bacteria and one Gram-negative bacterium...
  13. doi Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra
    Nicole Horstmann
    Institut für Organische Chemie, Ruprecht Karls Universität Heidelberg, Im Neuenheimer Feld 270, D 69120 Heidelberg, Germany
    J Nat Prod 74:1100-5. 2011
    ..iso-Archazolid B presents the most potent archazolid known...
  14. doi Modular total synthesis of rhizopodin: a highly potent G-actin dimerizing macrolide
    Manuel Kretschmer
    Institut fur Organische Chemie, Universitat Heidelberg, INF 270, 69120 Heidelberg Germany Current address Columbia University, New York, NY USA
    Chemistry 19:15993-6018. 2013
    ..This modular route will be amenable to the development of syntheses of other analogues of rhizopodin...
  15. doi Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones
    Michael Morgen
    University of Heidelberg, Department of Organic Chemistry, INF 270, D 69120 Heidelberg, Germany
    Org Lett 12:4494-7. 2010
    ..The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines...
  16. doi Diastereodivergent aldol reactions of beta-alkoxy ethyl ketones: modular access to (1,4)-syn and -anti polypropionates
    Fatih Arikan
    University of Heidelberg, Department of Organic Chemistry, INF 270, 69120 Heidelberg, Germany
    Org Lett 10:3521-4. 2008
    ..To achieve good selectivities in this diastereodivergent approach, selection of the protective group on the beta-oxygen of the enolate (R (2)) was of critical importance...
  17. ncbi On the verge of axial chirality: atroposelective synthesis of the AB-biaryl fragment of vancomycin
    Gerhard Bringmann
    Institut fur Organische Chemie, Universitat Wurzburg, Am Hubland, D 97074 Wurzburg, Germany
    Org Lett 4:2833-6. 2002
    ..Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution...
  18. doi Efficient synthesis of diverse hetero-bis-metallated alkenes as modular reagents towards highly conjugated and isolated olefinic systems
    Mario Altendorfer
    University of Heidelberg, Department of Organic Chemistry, INF 270, D 69120 Heidelberg, Germany, EU
    Chem Commun (Camb) 48:8267-9. 2012
    ..The utility of these reagents was further demonstrated in a concise and modular construction of extended polyene side chains of the potent polyketide antibiotic etnangien...
  19. doi Cycloadditions in the total synthesis of sporolide B
    Pengfei Li
    Institut fur Organische Chemie, Ruprecht Karls Universitat Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
    Angew Chem Int Ed Engl 48:5078-80. 2009
    ..These approaches should be considered in complex target syntheses...
  20. doi Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin
    Manuel Kretschmer
    Universitat Heidelberg, Institut fur Organische Chemie, INF 270, D 69120 Heidelberg, Germany
    Org Lett 14:382-5. 2012
    ..This route demonstrates the applicability of these methodologies in complex natural product synthesis...
  21. ncbi Atropo-enantioselective total synthesis of knipholone and related antiplasmodial phenylanthraquinones
    Gerhard Bringmann
    Institut fur Organische Chemie, Universitat Wurzburg, Am Hubland, D 97074 Wurzburg, Germany
    J Org Chem 67:5595-610. 2002
    ..The synthetic availability of these natural biaryls, their precursors, and their unnatural analogs permitted a broader investigation of the antiplasmodial activities of these interesting biaryls...
  22. doi Total synthesis and antibacterial activity of dysidavarone A
    Björn Schmalzbauer
    Kekule Institut fur Organische Chemie und Biochemie, University of Bonn, Gerhard Domagk Str 1, 53121 Bonn, Germany
    Org Lett 15:964-7. 2013
    ..Dysidavarone A showed potent antimicrobial and antiproliferative activities based on characteristic morphological changes of treated cells...
  23. ncbi Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra
    Jorma Hassfeld
    Gesellschaft fur Biotechnologische Forschung mbH, Medizinische Chemie and Umweltmikrobiologie, Mascheroder Weg 1, D 38124 Braunschweig, Germany
    Org Lett 8:4751-4. 2006
    ....
  24. ncbi Total synthesis of archazolid A
    Dirk Menche
    Helmholtz Zentrum für Infektionsforschung, Medicinal Chemistry, Inhoffenstrasse 7, 38124 Braunschweig, Germany
    J Am Chem Soc 129:6100-1. 2007
  25. ncbi Gaboroquinones A and B and 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside, phenylanthraquinones from the roots of Bulbine frutescens
    Berhanu M Abegaz
    Department of Chemistry, University of Botswana, Private Bag 0022, Gaborone, Botswana
    J Nat Prod 65:1117-21. 2002
    ..Compounds 2, 3, and 4 showed moderate to good antiplasmodial and antitrypanosomal activities in vitro...
  26. ncbi Synthesis of novel 11-desmethyl analogues of laulimalide by Nozaki-Kishi coupling
    Ian Paterson
    University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U K
    Org Lett 6:1293-5. 2004
    ..This methodology should allow modular introduction of other, unnatural, side chains. [reaction: see text]..
  27. ncbi Design, synthesis and biological evaluation of novel, simplified analogues of laulimalide: modification of the side chain
    Ian Paterson
    University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK, EU
    Bioorg Med Chem Lett 15:2243-7. 2005
    ....
  28. ncbi The first hydroxylated archazolid from the myxobacterium Cystobacter violaceus: isolation, structural elucidation and V-ATPase inhibition
    Dirk Menche
    Helmholtz Zentrum für Infektionsforschung GmbH, Medicinal Chemistry and Chemical Biology, Braunschweig, Germany
    J Antibiot (Tokyo) 60:328-31. 2007
    ..This novel metabolite was evaluated for growth inhibition of murine connective tissue cells and V-ATPase inhibition in comparison to other known archazolids...
  29. ncbi Directed reductive amination of beta-hydroxy-ketones: convergent assembly of the ritonavir/lopinavir core
    Dirk Menche
    Gesellschaft fur Biotechnologische Forschung mbH, Medizinische Chemie, Mascheroder Weg 1, D 38124 Braunschweig, Germany
    Org Lett 9:267-70. 2007
    ..The method was expanded to an asymmetric aldol reductive amination sequence to allow a highly convergent synthesis of the hydroxy-amine core of the HIV-protease inhibitors ritonavir and lopinavir. [reaction: see text]...
  30. doi Simultaneous determination of the conformation and relative configuration of archazolide a by using nuclear overhauser effects, J couplings, and residual dipolar couplings
    Christophe Fares
    Max Planck Institute for Biophysical Chemistry, NMR Based Structural Biology, Am Fassberg 11, 37077 Gottingen, Germany
    Angew Chem Int Ed Engl 47:3722-6. 2008
  31. ncbi Design, synthesis, and biological evaluation of novel analogues of archazolid: a highly potent simplified V-ATPase inhibitor
    Dirk Menche
    Helmholtz Zentrum für Infektionsforschung GmbH, Medizinische Chemie, Inhoffenstrasse 7, 38124 Braunschweig, Germany
    Bioorg Med Chem Lett 17:1732-5. 2007
    ....
  32. ncbi Efficient one-pot synthesis of biologically active polysubstituted aromatic amines
    Dirk Menche
    Helmholtz Zentrum für Infektionsforschung GmbH, Medizinische Chemie, Inhoffenstr 7, 38124 Braunschweig, Germany
    Bioorg Med Chem 15:7311-7. 2007
    ....
  33. ncbi Success in tubulysin D synthesis
    Florenz Sasse
    Nat Chem Biol 3:87-9. 2007