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Updated: Aug 27, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Expedited Total Synthesis of (±)-Brevianamide A via the Strategic Use of Gold(I) Catalysis
1Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Ontario, Canada.
Abstract:
Two concise and complementary routes to the polycyclic alkaloid (±)-brevianamide A from readily available amino acid building blocks are presented. Key to the synthesis is the strategic use of a gold(I)-catalyzed cascade process that quickly assembles the characteristic pseudoindoxyl motif of the natural product along with the two adjacent quaternary centers in a single step. This sequence, which exemplifies the structural complexity that can be achieved with gold catalysis, allowed for the shortest and highest-yield synthesis of (±)-brevianamide A to date (four steps LLS, 14% overall yield).
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