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Updated: Jun 15, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Total Synthesis of Brevianamide S.

Adam R Lockyer1, Helen E Jones1, Nicholas J Green1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.

Organic Letters
|March 28, 2025
PubMed
Summary

Scientists achieved the first total synthesis of brevianamide S, an alkaloid showing selective antibacterial activity against Mycobacterium tuberculosis surrogates. This breakthrough offers a new platform for developing novel antitubercular agents.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Natural Product Synthesis

Background:

  • Brevanamide S is a natural product isolated from Aspergillus versicolor.
  • It exhibits selective antibacterial activity against Bacille Calmette-Guérin (BCG).
  • BCG is a common surrogate for Mycobacterium tuberculosis.

Purpose of the Study:

  • To achieve the first total synthesis of brevianamide S.
  • To establish a flexible platform for synthesizing analogues.
  • To explore potential next-generation antitubercular agents.

Main Methods:

  • An eight-step synthetic route was developed.
  • A bidirectional synthetic strategy was employed.
  • Key reactions included a Stille cross-coupling and a double aldol condensation.

Main Results:

  • The first total synthesis of brevianamide S was successfully completed.
  • The synthesis was achieved in eight steps.
  • The methodology provides a flexible platform for analogue synthesis.

Conclusions:

  • The total synthesis of brevianamide S has been accomplished.
  • The developed synthetic platform enables the creation of diverse analogues.
  • Brevanamide S is a promising lead for developing new antitubercular drugs.