Abstract
Communesins, isolated from the mycelium of a strain of Penicillium sp., are cytotoxic heptacyclic indole alkaloids bearing a bis-aminal structure and two contiguous quaternary carbon centers. Toward a total synthesis of communesin F, we synthesized a pentacyclic ABCDG ring skeleton via carboborylation of 1,3-diene and a Friedel–Crafts-type cyclization, resulting in the formation of an azepine ring through a Bi(OTf)3-catalyzed SN2’ reaction.
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Acknowledgements
This work was supported by a Grant-in-Aid from JSPS KAKENHI (Grant Nos. JP17H05051 (CT), JP18H04407 (CT) and JP16H06384 (YT)) and a Grant-in-Aid from the Uehara Memorial Foundation, Japan (CT).
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Dedication: Dedicated to Professor SJ Danishefsky and his great contribution to total synthesis of highly complex and biologically important natural products.
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Nakajima, M., Tsukano, C., Yasui, M. et al. Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)3-catalyzed cyclizations. J Antibiot 72, 407–419 (2019). https://doi.org/10.1038/s41429-019-0142-7
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DOI: https://doi.org/10.1038/s41429-019-0142-7
