Yence, MerveAhmadli, DilgamSürmeli, DamlaKaracaoğlu, Umut MertPal, SujitTürkmen, Yunus Emre2025-02-182025-02-182024-12-232195-951Xhttps://hdl.handle.net/11693/116350Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45-90%). This cascade involves an initial Suzuki-Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C-H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[j]fluoranthenes, which are all structurally relevant to benzo[j]fluoranthene-based fungal natural products. The effectiveness of our strategy was demonstrated via a concise, four-step synthesis of the tetramethoxybenzo[j]fluoranthene derivative 18 , which represents a formal total synthesis of the fungal natural product bulgarein.EnglishCC BY 4.0 (Attribution 4.0 International Deed)https://creativecommons.org/licenses/by/4.0/Acenaphthylene-fused heteroarenesHeterocyclesFluoranthenesBenzo[j]fluoranthenesC–H arylationArticle10.3762/bjoc.20.2731860-5397