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Total Synthesis of Brevianamide S

Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide 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.
DOI: 10.1021/acs.orglett.5c00860
Authors: Adam R. Lockyer, Helen E. Jones, Nicholas J. Green, Robert C. Godfrey, Vera P. Demertzidou, Gary S. Nichol, Andrew L. Lawrence
Language: English
Field: Chemistry
Open Access status: hybrid
Estimated APC paid: $4,500
Funders: Diamond Light Source, European Commission, University of Edinburgh, University College Cork, Engineering and Physical Sciences Research Council, European Research Council, HORIZON EUROPE Marie Sklodowska-Curie Actions
Awards: G1687507451, G2367366709, G4515384058, Practical Organic Synthesis Inspired by Nature, G7363827314, A National Network for Applications of High-Field NMR in the Life and Physical Sciences, Gram-Scale Synthesis of Brevianamide Alkaloids.
OpenAlex ID: W4408920613
FWCI:
Cites: 23
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Related to: 10