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Expedited Total Synthesis of (±)-Brevianamide A via the Strategic Use of Gold(I) Catalysis.

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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).

Keywords: synthesis brevianamide; gold catalysis; use gold; synthesis; brevianamide; strategic use

Journal Title: Organic letters
Year Published: 2022

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