Orukotan, Will E, Knapper, Ben J, Dimitrova, Daniela et al. (1 more author) (2025) Modular Assembly of Macrocyclic Sulfonamides via Consecutive Cascade Ring Expansion Reactions. Chemistry : A European Journal. e02887. ISSN: 0947-6539
Abstract
Sulfur(IV) groups and macrocycles are both important motifs in bioactive molecules of significant current interest in medicinal chemistry, but methods for the efficient synthesis of macrocyclic sulfur(IV) compounds are rare. In this manuscript, a modular, versatile strategy for the synthesis of macrocyclic sulfonamides is described, using consecutive ring expansion reactions. First, linear starting materials are assembled from simple building blocks. This is followed by two distinct cascade ring expansion reaction steps performed in sequence. The utility of this modular approach is showcased via the synthesis of a library of 42 diversely functionalized 13- and 14-membered macrocyclic sulfonamides. The use of consecutive ring expansions is key to the success of the protocol, ensuring the products are formed in overall good yields without requiring high-dilution conditions.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2025 Wiley-VCH GmbH. This is an author-produced version of the published paper. Uploaded in accordance with the University’s Research Publications and Open Access policy. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Date Deposited: | 03 Oct 2025 08:30 |
Last Modified: | 03 Oct 2025 08:30 |
Published Version: | https://doi.org/10.1002/chem.202502887 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1002/chem.202502887 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:232517 |
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