Total Synthesis and 13C NMR Revision of Nagelamide C

Author(s)
Tong, Guanghu; Nguyen, Long V.; Jamison, Timothy F.
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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.
Date issued
2025-06-04
URI
https://hdl.handle.net/1721.1/164927
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Chemistry Frontiers
Publisher
Royal Society of Chemistry
Citation
Tong, Guanghu, Nguyen, Long V. and Jamison, Timothy F. 2025. "Total Synthesis and 13C NMR Revision of Nagelamide C." Organic Chemistry Frontiers, (20).
Version: Final published version
ISSN
2052-4129
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