Total Synthesis and 13C NMR Revision of Nagelamide C
Name
D5QO00721F.pdf
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1.13 MB
Format
Adobe PDF
Checksum (MD5)
bafe6f0a73eccfd7742949ca13fa1cd3
Author(s)
Tong, Guanghu
Nguyen, Long V.
Jamison, Timothy F.
Date Issued
June 4, 2025
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial
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DOI of Published Version
https://doi.org/10.1039/D5QO00721F
