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Updated: Jun 15, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
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.
Abstract:
The first total synthesis of the alkaloid brevianamide S has been achieved in eight steps. This natural product, isolated from Aspergillus versicolor, exhibits selective antibacterial activity against Bacille Calmette-Guérin (BCG), a commonly used surrogate for Mycobacterium tuberculosis. Brevianamide S is proposed to act through a novel, yet-to-be-elucidated mechanism, making it a promising lead in the development of next-generation antitubercular agents. Our approach employs a bidirectional synthetic strategy, involving a bespoke alkenyl-alkenyl Stille cross-coupling reaction and a double aldol condensation. This represents a flexible and efficient platform for the future synthesis of structurally diverse analogues.
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