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Related Experiment Videos

Synthesis of the vancomycin CDE ring system

D L Boger1, R T Beresis, O Loiseleur

  • 1Department of Chemistry, Scripps Research Institute, La Jolla, California 92037, USA.

Bioorganic & Medicinal Chemistry Letters
|January 1, 1999
PubMed
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This study presents the first synthesis of a vancomycin CDE ring system, establishing a method for controlling stereochemistry and suggesting an optimal order for ring formation in complex molecule synthesis.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Vancomycin is a critical antibiotic for treating serious bacterial infections.
  • The complex structure of vancomycin presents significant synthetic challenges.
  • Previous synthetic efforts have not fully addressed the CDE ring system.

Purpose of the Study:

  • To achieve the first synthesis of a functionalized vancomycin CDE ring system.
  • To develop a strategy for controlling the stereochemistry of the CDE atropisomers.
  • To establish a preferred order for macrocyclization in vancomycin synthesis.

Main Methods:

  • Utilized aromatic nucleophilic substitution reactions for sequential CD and DE macrocyclization.
  • Employed selective thermal equilibration for controlling CDE atropisomer stereochemistry.

Related Experiment Videos

  • Developed a protected and fully functionalized vancomycin CDE core.

    • Main Results:

    • Successfully synthesized the vancomycin CDE ring system with a C and E ring monochloro substitution pattern.
    • Demonstrated indirect control over CDE atropisomer stereochemistry via thermal equilibration.
    • Established a rationale for the order of CD and DE ring system introduction.

    Conclusions:

    • The developed synthetic route provides a viable pathway to the vancomycin CDE core.
    • The method offers a novel approach to controlling atropisomer stereochemistry in complex molecules.
    • The findings inform future strategies for vancomycin total synthesis and analog development.