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Synthesis of the Proposed Structure of Celacarfurine and Analogues Using Sequential Cascade Ring Expansion Reactions

Lookup NU author(s): Alexandra Longcake, Professor Mike ProbertORCiD

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Abstract

The first synthesis of the proposed structure of spermidine derived macrocyclic alkaloid celacarfurine is described. A versatile synthetic strategy has been developed based on sequential cascade ring expansion reactions, with high dilution conditions not needed for any of the steps. The same general strategy was also used to generate a series of macrocyclic analogues. The physical properties and spectroscopic data obtained for our synthetic product do not match those reported for the isolated alkaloid.

Publication metadata

Author(s): Tam JKF, Waddell LJN, Palate KY, Whitwood AC, Longcake A, Probert MR, Grogan G, Lichman BR, Unsworth WP

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2026

Volume: 28

Issue: 4

Pages: 1441-1446

Print publication date: 30/01/2026

Online publication date: 20/01/2026

Acceptance date: 12/01/2026

Date deposited: 16/02/2026

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society

URL: https://doi.org/10.1021/acs.orglett.5c05328

DOI: 10.1021/acs.orglett.5c05328

Data Access Statement: The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.5c05328

PubMed id: 41559892

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