Total Synthesis of (-)-Psathyrin A Enabled by Radical Cyclization.

ABSTRACT: We report herein an enantioselective total synthesis of (-)-psathyrin A, an antibacterial diterpene natural product possessing a unique 6/4/5/5 tetracyclic carbon skeleton and seven contiguous stereocenters, including three adjacent all-carbon quaternary centers. Our synthesis begins with commercially available 2-methyl-2-cyclopenten-1-one, which was subjected to an enantioselective copper/NHC-catalyzed conjugate addition, followed by trapping the resulting enolate with 1-bromo-2-butyne to set up the first two stereocenters, including one all-carbon quaternary center. A Suzuki-Miyaura cross coupling introduces an aromatic ring as the six-membered ring precursor, and a gold(I)-catalyzed Conia-ene reaction constructs the 5/5-fused bicyclic ring system and the second all-carbon quaternary cen

SUBMITTER: Zhao W 

PROVIDER: S-EPMC12426916 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature