Total Synthesis and 13C NMR Revision of Nagelamide C

Abstract

Nagelamide C (1), a dimeric pyrrole−imidazole alkaloid, exhibits antimicrobial and antibacterial activities. We demonstrate herein the first total synthesis of nagelamide C. This concise work was enabled by a series of significant transformations featuring: an imidazole benzylic Wittig olefination, a site selective bromination, and a regioselective trans-hydrostannylation/Stille coupling to construct a unique trisubstituted olefin. In addition, we show the original 13C NMR data of nagelamide C to be in error and revise the data.

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Article information

Article type
Research Article
Submitted
06 May 2025
Accepted
04 Jun 2025
First published
05 Jun 2025
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2025, Accepted Manuscript

Total Synthesis and 13C NMR Revision of Nagelamide C

G. Tong, T. F. Jamison and L. V. Nguyen, Org. Chem. Front., 2025, Accepted Manuscript , DOI: 10.1039/D5QO00721F

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