Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles

Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles
Shinya Oishi, Junpei Matsuoka, Yuka Matsuda, Yuiki Kawada, Hiroaki Ohno
In total and formal syntheses of dictyodendrins B, C, E, and F, the key step involved the direct construction of the pyrrolo[2,3-c]carbazole core by the gold-catalyzed annulation of a conjugated diyne with a pyrrole to form three bonds and two aromatic rings. The subsequent introduction of substituents at the C1 (Suzuki–Miyaura coupling), C2 (addition to an aldehyde), N3 (alkylation), and C5 positions (Ullman coupling) provided divergent access to dictyodendrins. Why settle for one? In total and formal syntheses of dictyodendrins B, C, E, and F, the key step was the direct construction of the tetracyclic pyrrolo[2,3-c]carbazole core by the gold-catalyzed annulation of a conjugated diyne with a pyrrole (see scheme). This synthetic route could be used for the diversity-oriented synthesis of dictyodendrin derivatives for medicinal applications.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703279

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