Total Synthesis of (±)-Integerrines B–F via Bismuth-Catalyzed Oxidative Homo- and Cross-Couplings of 3-Hydroxycarbazoles

The total synthesis of (±)-integerrine B and the first total synthesis of (±)-integerrine C–F were realized, and 30–65% yields were achieved over 1–6 step(s) from the corresponding 3-hydroxycarbazole monomers. The key step involved the chemo- and regioselective bismuth-catalyzed oxidative homo- and cross-couplings of 3-hydroxycarbazoles with m-chloroperbenzoic acid. This strategy not only provides access to oxygen-sensitive biaryl alkaloids but also establishes a foundation for future asymmetric syntheses and broader applications in biaryl natural products.