# Total Synthesis of Brevianamide S

## TL;DR

Scientists synthesized a natural compound called brevianamide S, which shows potential as a new type of tuberculosis treatment.

## Contribution

The first total synthesis of brevianamide S using a bidirectional strategy with novel cross-coupling and aldol reactions.

## Key findings

- Brevianamide S was synthesized in eight steps from Aspergillus versicolor.
- The compound shows selective antibacterial activity against BCG, a tuberculosis surrogate.
- The synthesis method allows for creating diverse analogs for drug development.

## 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.