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DOI: 10.1055/a-2079-9411
Palladium-Catalyzed Cyanation of Nucleobases: Total Synthesis of Toyocamycin, Sangivamycin, and a Mycalisine A Precursor
This work has been funded by Rasayan Inc., USA.
Abstract
Installation of cyano group functionality onto nucleosides has always been a challenging task for chemists, and catalytic protocols developed for simple aryl substrates have, in most cases, failed to replicate their success when applied to nucleobase or sugar moieties of nucleosides. Given the importance of the cyano and amide functionalities in nucleoside chemistry, we herein disclose an efficient Pd-catalyzed cyanation protocol specifically applied to iodo nucleobases. Furthermore, the developed cyanation method has been explored for the synthesis of naturally occurring and bioactive nucleosides such as toyocamycin, sangivamycin, and a mycalisine A precursor.
Key words
nucleosides - toyocamycin - sangivamycin - palladium catalysis - cyanation - late-stage modificationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2079-9411.
- Supporting Information
Publikationsverlauf
Eingereicht: 22. März 2023
Angenommen nach Revision: 24. April 2023
Accepted Manuscript online:
24. April 2023
Artikel online veröffentlicht:
25. Mai 2023
© 2023. Thieme. All rights reserved
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