Total synthesis and 13C NMR revision of nagelamide C

Guanghu Tong; Long V. Nguyen; Timothy F. Jamison

doi:10.1039/D5QO00721F

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Total synthesis and ¹³C NMR revision of nagelamide C†

Guanghu Tong,

‡*^a Long V. Nguyen^a and Timothy F. Jamison

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* Corresponding authors

^a Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 77 Massachusetts 02139, USA

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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DOI: https://doi.org/10.1039/D5QO00721F
Article type: Research Article
Submitted: 06 May 2025
Accepted: 04 Jun 2025
First published: 05 Jun 2025
This article is Open Access

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Org. Chem. Front., 2025, Advance Article

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Total synthesis and ¹³C NMR revision of nagelamide C

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

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