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October 16, 1998Angewandte Chemie International Edition

Total Syntheses of Vancomycin and Eremomycin Aglycons

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Authors

DEDavid A. EvansBoston CollegeMWMichael R. WoodNorth Carolina State UniversityBTB. Wesley TrotterMerck & Co., Inc., Rahway, NJ, USA (United States)

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Implication

Synthetic chemistry study demonstrates the total syntheses of vancomycin and eremomycin aglycons, highlighting conformational control in macrocyclization.

Key Points

  • Achieve the first total chemical syntheses of vancomycin and eremomycin aglycons by controlling planar and axial chirality during core macrocyclizations.
  • Designed total synthetic routes targeting the complex aglycon frameworks of vancomycin and eremomycin.
  • Evaluated the impact of substrate structural features on the kinetic and thermodynamic regulation of atropselective macrocyclization reactions.
  • Completed the first total syntheses of both the vancomycin and eremomycin aglycons.
  • Determined how structural elements dictate kinetic versus thermodynamic outcomes during atropselective macrocyclic ring closures.

Cite This Study

Evans et al. (1998) studied this question.

synapsesocial.com/papers/6a95d0d66823ee7bfe514464https://doi.org/10.1002/(sici)1521-3773(19981016)37:19<2700::aid-anie2700>3.0.co;2-p
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