Literature DB >> 29711601

Total Syntheses of Vancomycin and Eremomycin Aglycons.

David A Evans1, Michael R Wood1, B Wesley Trotter1, Timothy I Richardson1, James C Barrow1, Jeffrey L Katz1.   

Abstract

Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin-resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Antibiotics; Eremomycin; Natural products; Total synthesis; Vancomycin

Year:  1998        PMID： 29711601     DOI： 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  21 in total

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4.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

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7.  Next-Generation Total Synthesis of Vancomycin.

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Review 8.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
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Review 9.  Biological, chemical, and biochemical strategies for modifying glycopeptide antibiotics.

Authors:  Edward Marschall; Max J Cryle; Julien Tailhades
Journal:  J Biol Chem       Date:  2019-10-31       Impact factor: 5.157

10.  Total synthesis and evaluation of [Psi[CH2NH]Tpg4]vancomycin aglycon: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

Authors:  Brendan M Crowley; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419
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