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Synlett 2024; 35(06): 654-658
DOI: 10.1055/a-2079-9411
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Special Issue to Celebrate the Centenary Year of Prof. Har Gobind Khorana

Palladium-Catalyzed Cyanation of Nucleobases: Total Synthesis of Toyocamycin, Sangivamycin, and a Mycalisine A Precursor

Harshita Shet
a   Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh Road, Matunga, Mumbai-400019, India
,
Rajesh Sahu
a   Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh Road, Matunga, Mumbai-400019, India
,
Yogesh S. Sanghvi
b   Rasayan Inc., 2802, Crystal Ridge, Encinitas, CA 92024-6615, USA
,
Anant R. Kapdi∗
a   Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh Road, Matunga, Mumbai-400019, India
› Author AffiliationsThis work has been funded by Rasayan Inc., USA.
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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 modification

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2079-9411.
  • Supporting Information


Publication History

Received: 22 March 2023

Accepted after revision: 24 April 2023

Accepted Manuscript online:
24 April 2023

Article published online:
25 May 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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