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Catalytic Asymmetric Synthesis of Mixed 3,3′-Bisindoles and Their Evaluation as Wnt Signaling Inhibitors


  • We thank Prof. Jeremy Nathans (Johns Hopkins Medical School) for kindly offering the STF/293 cells and Prof. Randall T. Moon (University of Washington) for the Super TOP-Flash and Super FOP-Flash reporter plasmids. This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan), Daiichi-Sankyo Foundation of Life Science, and a Workshop on Chirality in Chiba University (WCCU).


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TOP class: The first efficient catalytic asymmetric coupling reaction of indoles with isatin-derived nitroalkenes was accomplished by using a complex consisting of a chiral imidazoline aminophenol ligand (1; see scheme) and Cu(OTf)2. Biological activity of the newly formed chiral 3,3′-bisindoles was also confirmed in a Wnt signaling inhibitory assay.