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… Click to show full 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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